Oxalyl chloride → HCID 66605334, compound

Step 2 A solution of crude 2-(bromomethyl)-5-fluorobenzoic acid (3.05 g, 13.1 mmol) in DCM (50 mL) was treated with oxalyl chloride (1.66 g, 13.1 mmol) and 6 drops of DMF. The mixture was stirred at rt for 1 h, then was concentrated. The residue was redissolved in DCM (50 mL) and treated with 3-bromo-2-methylaniline (1.705 g, 9.16 mmol). The mixture was stirred at rt for 1 h, then TEA (2.19 mL, 15.7 mmol) was added in portions. The mixture was stirred at rt for 2 h, then was diluted with DCM (100 mL), washed with NaHCO3 (aq) and water, dried and concentrated. The residue was triturated with DCM to provide N-(3-bromo-2-methylphenyl)-2-(bromomethyl)-5-fluorobenzamide as a white solid (0.9 g). The mother liquor was concentrated and the residue was again triturated with DCM to provide additional N-(3-bromo-2-methylphenyl)-2-(bromomethyl)-5-fluorobenzamide as a white solid (0.46 g). The mother liquor was concentrated and the residue was purified by column chromatography (eluting with a gradient from hexane to 70:30 EtOAc-hexane) to provide additional N-(3-bromo-2-methylphenyl)-2-(bromomethyl)-5-fluorobenzamide as a pink solid (1.18 g) for a total of 2.54 g (48%). Mass spectrum m/z 400, 402, 404 (M+H)+.

1. concentrationwas concentrated
2. dissolutionThe residue was redissolved in DCM (50 mL)
3. stirringThe mixture was stirred at rt for 1 h
4. stirringThe mixture was stirred at rt for 2 h
5. washwashed with NaHCO3 (aq) and water
6. customdried
7. concentrationconcentrated
8. customThe residue was triturated with DCM

ORD record

ord-7b174c280bd94f82aa48ec0abe8c4917

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084620B2