(Dimethyl sulfide)trihydroboron → Methyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 14121

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5](O)=[O:6].CSC.B>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To an ice-cold, stirred solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (5.0 g, 19.3 mmol) in tetrahydrofuran (77.2 mL) is added borane dimethyl sulfide complex (10.6 mL, 2.0 M tetrahydrofuran, 21.1 mmol). The reaction mixture is heated at 50° C. for 2 h. The reaction mixture is quenched with methanol (50 mL) and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H), 7.90 (s, 1H), 7.69 (s, 1H), 4.69 (s, 1H), 3.91 (s, 3H), 2.83 (br s, 1H).

Workup

customThe reaction mixture is quenched with methanol (50 mL)
concentrationconcentrated under reduced pressure
customPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-6ab5802c15eb4630b4c347d78572be51
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727997B2

Linked notes

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