Acetic Acid → 1-Bromo-3,5-bis(trifluoromethyl)benzene
Reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=1.C(O)(=O)C.S(=O)(=O)(O)O.[Br:24]N1C(C)(C)C(=O)N(Br)C1=O>O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:8]=[C:7]([Br:24])[CH:6]=[C:5]([C:9]([F:10])([F:11])[F:12])[CH:4]=1Participants
6
Conditions
- Temperature
- 40 °C
Procedure
A vigorously stirred solution of 1,3-bis(trifluoromethyl)benzene (107 g) in a mixture of glacial acetic acid (22 mL) and concentrated sulfuric acid (142 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (77.25 g) at 25° C. The exothermic reaction raised the temperature to approximately 40° C. After aging at 45° C. for 4.5 h, the mixture was cooled to approximately 0° C. and poured into cold water (250 mL). After washing with 5N NaOH (75 mL) the organic layer contained 137 g of the desired 3,5-bis(trifluoromethyl)-1-bromobenzene by assay (94% yield). This product was used in the next step without further purification.
Workup
- customThe exothermic reaction
- temperaturethe mixture was cooled to approximately 0° C.
- washAfter washing with 5N NaOH (75 mL) the organic layer
- customThis product was used in the next step without further purification
Sources & evidence
- ORD record
- ord-422519bee1af4558aa63dcba1d5d587c
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06600040B2
Reaction notes
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