C1N=CN(C(N2C=NC=C2)=O)C=1.C1COCC1.[Br:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[C:21](O)=[O:22].[BH4-].[Na+]>CCOC(C)=O.C([O-])(O)=O.[Na+].O>[Br:18][C:19]1[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24][C:20]=1[CH2:21][OH:22]Solid CDI (4.3 g, 26.4 mmol) was added to a THF solution (130 mL) of 2-bromo-4,5-difluorobenzoic acid and the solution was refluxed. After 3 h the resulting mixture was cooled to room temperature and a water solution (26 mL) of NaBH4 (666 mg, 17.6 mmol) was added. After 10 min the resulting mixture was diluted with EtOAc and 10% aqueous NaHCO3 and the layers were separated. The organic layer was washed with water and brine, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.
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