Borane;tetrahydrofuran → HCID 14033036, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution/suspension of 3-chloro-5-methylbenzoic acid (800 mg, 4.69 mmol) in THF (5 ml) at 0° C. under nitrogen was added dropwise borane tetrahydrofuran complex (1 M in THF, 23.45 ml, 23.45 mmol) over 30 mins maintaining the temperature around 0° C. The reaction mixture was then allowed to warm to RT over 20 hrs. On cooling in an ice/water bath the reaction mixture was quenched dropwise with water and after a few minutes the THF was removed under reduced pressure. Water was added to the residue and on cooling a few drops of 1M HCl were added until effervescence ceased. The mixture was diluted with water and extracted into EtOAc, the organic portion dried over MgSO4, filtered and concentrated under reduced pressure. Purification was carried out by chromatography on silica using 0-50% EtOAc in hexanes as eluent and azeotroping with toluene to afford the title product.

Provenance & Evidence