Sulfuric Acid → N-[3-(2-Bromoacetyl)-5-(pentafluorosulfanyl)phenyl]acetamide
Reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([S:10]([F:15])([F:14])([F:13])([F:12])[F:11])[CH:9]=1)(=[O:3])[CH3:2].[Br-:20].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.S(=O)(=O)(O)O>CO.C1COCC1>[Br:20][CH2:2][C:1]([C:4]1[CH:5]=[C:6]([NH:16][C:17](=[O:19])[CH3:18])[CH:7]=[C:8]([S:10]([F:11])([F:12])([F:13])([F:14])[F:15])[CH:9]=1)=[O:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
N-[3-Acetyl-5-(pentafluorosulfanyl)phenyl]acetamide (859 mg, for synthesis see example 1) was dissolved in a mixture of methanol (10 ml) and THF (10 ml) and phenyltrimethylammonium tribromide (1.065 g) was added in portions while stirring. After stirring at RT for 2 h, the mixture was heated to 40° C. for a further 3 h. After cooling, the reaction mixture was added to 2 N sulfuric acid and the aqueous phase was extracted 3 times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated. The crude product was purified using silica gel with ethyl acetate/heptane as the eluent. 480 mg of the desired compound were obtained. LC-MS rt: 1.47 min [M+H]+: 382.0 (met. a)
Workup
- additionwas added in portions
- stirringAfter stirring at RT for 2 h
- temperatureAfter cooling
- extractionthe aqueous phase was extracted 3 times with ethyl acetate
- dry with materialThe combined extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified
Sources & evidence
- ORD record
- ord-ca8c04a6469642f782566b43976da55b
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08198272B2
Reaction notes
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