Cesium fluoride → Butyl 2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662319노트

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HRID 1662319 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1B(O)O.[F-].[Cs+].Br[C:16]1[CH:28]=[CH:27][C:19]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])=[CH:18][C:17]=1[O:29][CH2:30][CH2:31][CH2:32][CH3:33]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[CH2:30]([O:29][C:17]1[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH2:24][CH2:25][CH3:26])=[O:21])[CH:27]=[CH:28][C:16]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1])[CH2:31][CH2:32][CH3:33]

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 41572112-Fluoro-5-methoxyphenylboronic acidHCID 57467609Butyl 4-bromo-3-(butyloxy)benzoate

생성물 1

HCID 57705770Butyl 2-(butyloxy)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate수율 67.6%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 80711,2-Dimethoxyethane용매

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온도
90 °C

실험 절차

To a 2 dram vial charged with 2-fluoro-5-methoxyphenylboronic acid (available from Aldrich) (2.323 g, 13.67 mmol), tetrakis(triphenylphosphine) palladium(0) (0.7897 g, 0.6834 mmol), cesium fluoride (0.8409 mL, 22.78 mmol), and 5.1 (1.50 g, 4.556 mmol), was added DME (20 mL), and the mixture was then heated at 90° C. overnight. The reaction was allowed to cool and then filtered and concentrated. The crude product was purified by combiflash (0 to 10% EtOAc/hexanes) yielding 5.2 (1.1530 g, 67.58% yield).

후처리

  1. temperatureto cool
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude product was purified by combiflash (0 to 10% EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-68d7f414a57f45ee96003437450809bf
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030354B2

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