Cesium carbonate → 2-Acetyl-4-[2-(2,2,2-trifluoroethoxy)-3-tert-butyl-5-methylphenyl]benzo[b]thiophene

HRID 1394614

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HRID 1394614 반응식
[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=3[OH:24])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2].[F:25][C:26]([F:30])([F:29])[CH2:27]Br.C([O-])([O-])=O.[Cs+].[Cs+].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[C:17]([CH3:19])[CH:16]=[C:15]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:14]=3[O:24][CH2:27][C:26]([F:30])([F:29])[F:25])[C:6]=2[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 678982-Bromo-1,1,1-trifluoroethaneHCID 179528022-Acetyl-4-(2-hydroxy-3-tert-butyl-5-methylphenyl)benzo[b]thiopheneHCID 21226206Ethyl acetate hexane

생성물 1

HCID 596820732-Acetyl-4-[2-(2,2,2-trifluoroethoxy)-3-tert-butyl-5-methylphenyl]benzo[b]thiophene수율 71%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 211 mg (0.63 mmol) of 2-acetyl-4-(2-hydroxy-3-tert-butyl-5-methylphenyl)benzo[b]thiophene, 0.1 ml (132 mg, 0.81 mmol) of 1,1,1-trifluoro-2-bromoethane and 304 mg (0.94 mmol) of Cs2CO3 in 2.5 ml of dry DMF was heated at 60° C. in a pressure tube overnight. After cooling at room temperature, 10 mL of a 5/95 ethyl acetate/hexane solution was added and the remaining mixture was stirred for 5 minutes. The solution was filtrated through a silica plug (eluent: 5/95 ethyl acetate/hexane) and the solvents were removed under pressure. 188 mg (0.44 mmol, yield: 71%) of 2-acetyl-4-[2-(2,2,2-trifluoroethoxy)-3-tert-butyl-5-methylphenyl]benzo[b]thiophene was isolated as an oil. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=7.9 Hz, 1H), 7.75 (s, 1H), 7.54 (t, J=7.8 Hz, 1H), 7.45 (d, J=7.9 Hz, 1H), 7.26 (d, J=1.9 Hz, 1H), 7.06 (d, J=1.9 Hz, 1H), 3.63 (m, 1H), 3.52 (m, 1H), 2.56 (s, 3H), 2.38 (s, 3H), 1.48 (s, 9H).

후처리

  1. temperatureAfter cooling at room temperature
  2. filtrationThe solution was filtrated through a silica plug (eluent: 5/95 ethyl acetate/hexane)
  3. customthe solvents were removed under pressure

출처 및 근거

ORD 기록
ord-d2be93b7c53f4b68ab1c91204abe97ec
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07348359B2

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