Lithium borohydride → (5-Chloro-2-(methylsulfonyl)phenyl)methanol

HRID 1015696Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[BH4-].[Li+]>O1CCCC1CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([CH2:7][OH:8])[CH:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

(Step 2) To a solution of methyl 5-chloro-2-(methylsulfonyl)benzoate obtained in Step 1 (2.65 g) in tetrahydrofuran-ethanol (50 ml+5 ml) was added lithium borohydride (348 mg) at 0° C. The mixture was stirred at 60° C. for 2 hr, treated with ice, and extracted with ethyl acetate. The extract was washed successively with 1N hydrochloric acid and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1) to give [5-chloro-2-(methylsulfonyl)phenyl]methanol (2.1 g).

Workup

additiontreated with ice
extractionextracted with ethyl acetate
washThe extract was washed successively with 1N hydrochloric acid and saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record: ord-90ddb0e3b8184d4b967e30e80fe09290
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985862B2

Reaction notes

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