Water → 2-Hydroxy-4-(methylsulfonyl)benzoic acid

HRID 452446Notes

Reaction equation

B(Br)(Br)Br.C[O:6][C:7]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].O>C(Cl)Cl>[OH:6][C:7]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1.0 M boron tribromide (44.0 ml, 44.0 mmol) in DCM (20 ml) was cooled to 0° C. 2-methoxy-4-(methylsulfonyl)benzoic acid (4.0 g, 17.4 mmol) dispergated in DCM (120 ml) was slowly added to the tribromide-solution during 20 minutes. The reaction mixture was vigorously stirred for 1.5 h at 0° C. Water was added and the organic phase was separated. The aqueous phase was extracted with DCM and EtOAc. The combined organic phases was dried (Na2SO4) and evaporated under reduced pressure to give a white powder (3.6 g). 1H-NMR (400 MHz, MeOH): δ 8.07 (1H, d, J 8.0 Hz), 7.42 (1H, d, J 2.0 Hz), δ 7.38 (1H, dd, J1 8.4 Hz, J2 1.6 Hz), δ 3.11 (3H, s).

Workup

customthe organic phase was separated
extractionThe aqueous phase was extracted with DCM and EtOAc
dry with materialThe combined organic phases was dried (Na2SO4)
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-fc6f63d96a6b482c8c9e53f34771cdc8
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492372B2

Reaction notes

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