Benzoic acid, 2,5-dichloro-4-fluoro- → HCID 54012777, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:3]=1[C:4](O)=[O:5]>C1COCC1>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([Cl:12])=[CH:7][C:3]=1[CH2:4][OH:5]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,5-dichloro-4-fluorobenzoic acid (4.1 g, 19.6 mmol; prepared as described in the literature: Feit, P. W. et al, J. Med. Chem. 1972, Vol. 15, 79-83) in 100 mL THF was treated with 24.5 mL borane methylsulfide complex in THF (2M, 24.5 mL, 49 mmol) at 0-5° C. The mixture was allowed to come to RT, stirred for 14 h at RT and quenched by adding saturated NaHCO3 and 10 mL MeOH. The mixture was extracted with ethyl acetate, the organic layer was washed sequentially with 10% HCl and saturated NaHCO3 solutions, dried over magnesium sulfate and concentrated to give 3.65 g of the title compound as a white solid. ##STR265##