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

HRID 1662319ノート

反応式

HRID 1662319 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-68d7f414a57f45ee96003437450809bf
出典データセット
uspto-grants-2011_10
特許番号
US08030354B2

反応ノート

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