1-溴-4-氯-2-(甲氧基甲氧基甲基)苯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 18d in the same manner as compound 19b: mp 142-144° C. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.96 (s, 2H), 7.38 (d, J=7.8 Hz, 1H), 7.49 (s, 1H), 7.71 (d, J=7.8 Hz, 1H), 9.30 (s, 1H); ESI-MS m/z 167 (M−H)−; HPLC purity 99.0%; Anal (C7H6ClO2.0.1H2O)C, H.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-4-fluorobenzoic acid in the same manner as compound 18d and was used for the next step without purification. was used for the next step without purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-6-fluorobenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.43 (s, 3H), 4.74 (s, 2H), 4.76 (d, J=2.1 Hz, 2H), 7.05 (t, J=9.1 Hz, 1H), 7.18 (td, J=8.2, 5.9 Hz, 1H), 7.40 (d, J=8.2 Hz, 1H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-4,5-difluorobenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.42 (s, 3H), 4.57 (d, J=1.2 Hz, 2H), 4.76 (s, 2H), 7.3-7.5 (m, 2H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-5-methoxybenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, DMSO-d6): δ 3.30 (s, 1H), 3.74 (s, 3H), 4.50 (s, 2H), 4.69 (s, 2H), 6.83 (dd, J=8.8, 2.9 Hz, 1H), 7.40 (d, J=2.9 Hz, 1H), 7.48 (d, J=8.8 Hz, 1H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-5-methylbenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, DMSO-d6) δ (ppm) 2.27 (s, 3H), 3.30 (s, 3H), 4.51 (s, 2H), 4.68 (s, 2H), 7.05 (dd, J=7.9, 2.3 Hz, 1H), 7.30 (d, J=1.5 Hz, 1H), 7.46 (d, J=8.2 Hz, 1H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 18d in the same manner as compound 19b: mp 142-144° C. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.96 (s, 2H), 7.38 (d, J=7.8 Hz, 1H), 7.49 (s, 1H), 7.71 (d, J=7.8 Hz, 1H), 9.30 (s, 1H); ESI-MS m/z 167 (M−H)−; HPLC purity 99.0%; Anal (C7H6ClO2.0.1H2O)C, H.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 18d in the same manner as compound 19b: mp 142-144° C. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 4.96 (s, 2H), 7.38 (d, J=7.8 Hz, 1H), 7.49 (s, 1H), 7.71 (d, J=7.8 Hz, 1H), 9.30 (s, 1H); ESI-MS m/z 167 (M−H)−; HPLC purity 99.0%; Anal (C7H6ClO2.0.1H2O)C, H.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-4-fluorobenzoic acid in the same manner as compound 18d and was used for the next step without purification. was used for the next step without purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-6-fluorobenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.43 (s, 3H), 4.74 (s, 2H), 4.76 (d, J=2.1 Hz, 2H), 7.05 (t, J=9.1 Hz, 1H), 7.18 (td, J=8.2, 5.9 Hz, 1H), 7.40 (d, J=8.2 Hz, 1H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-4,5-difluorobenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.42 (s, 3H), 4.57 (d, J=1.2 Hz, 2H), 4.76 (s, 2H), 7.3-7.5 (m, 2H).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was made from 2-bromo-4,5-difluorobenzoic acid in the same manner as compound 18d: 1H NMR (300 MHz, CDCl3) δ (ppm) 3.42 (s, 3H), 4.57 (d, J=1.2 Hz, 2H), 4.76 (s, 2H), 7.3-7.5 (m, 2H).