Ammonia → 4-Bromo-3-fluorobenzene-1-sulfonamide

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12].[NH3:13]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:13])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:12]

Participants

Reactant 2

HCID 222Ammonia

HCID 27782184-Bromo-3-fluorobenzenesulfonyl chloride

Product 1

HCID 27784044-Bromo-3-fluorobenzene-1-sulfonamide

Procedure

According to general procedure A, 4-Bromo-3-fluoro-benzenesulfonyl chloride (0.40 g, 1.46 mmol) and ammonia (20 mL, ca. 7N in methanol) were stirred together for 16 hours. 4-bromo-3-fluorobenzenesulfonamide was provided after purification (0.23 g, 61%). HRMS: calcd for C6H5BrFNO2S, 252.92084; found (EI, M+), 252.9201. HPLC purity 100.0% at 210-370 nm, 7.5 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

Sources & evidence

ORD record: ord-a3e706bae62e4e72a1b333e48c708669
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723332B2

Reaction notes

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