Boron tribromide → 2-Nitro-5-(phenylsulfonyl)phenol

HRID 2224053Notes

Reaction equation

[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([O:19]C)[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([OH:19])[CH:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-benzenesulfonyl-2-methoxy-1-nitro-benzene (4.69 g, 16 mmol) was dissolved in 250 mL of methylene chloride and cooled to 0° C. BBr3 (64 mL, 1M in methylene chloride) was added dropwise to the reaction mixture over 30 minutes. Stirring was continued, and the reaction mixture was allowed to warm up to room temperature. Methylene chloride (200 mL) was added to the reaction mixture and the organic layer was washed twice with 450 mL of water, once with 200 mL of saturated NaHCO3, dried (MgSO4) and concentrated in vacuo. The residue was recrystallized from ethanol to afford 3.206 g (11.5 mmol, 72%) of 5-benzenesulfonyl-2-nitro-phenol as a yellow solid. MS: 280 (M+H)+.

Workup

temperatureto warm up to room temperature
washthe organic layer was washed twice with 450 mL of water, once with 200 mL of saturated NaHCO3
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-d6199cf5c8144d3cac5fa87c8cd63d91
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07378415B2

Reaction notes

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