4-Fluorobenzoyl chloride → (4-Bromo-2-methoxy-5-methylphenyl)(4-fluorophenyl)methanone

HRID 1988191ノート

反応式

HRID 1988191 の反応式
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[Br:15][C:16]1[CH:17]=[C:18]([O:23][CH3:24])[CH:19]=[CH:20][C:21]=1[CH3:22]>ClCCCl>[Br:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)=[O:7])=[C:18]([O:23][CH3:24])[CH:17]=1

参加物

5

反応物 3

HCID 678794-Fluorobenzoyl chlorideHCID 5202882-Bromo-4-methoxy-1-methylbenzeneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 57729258(4-Bromo-2-methoxy-5-methylphenyl)(4-fluorophenyl)methanone

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

4-Fluorobenzoyl chloride (1.40 mL, 11.9 mmol) was added dropwise to a suspension of AlCl3 (1.73 g, 13.0 mmol) in 1,2-dichloroethane (30 mL) at room temperature. After 15 min a solution of 3-bromo-4-methylanisole (2.17 g, 10.8 mmol) in 1,2-dichloroethane (3 mL) was added dropwise. The resulting mixture was stirred for 2 h, poured into 200 mL of ice-water, stirred for 20 min and extracted with CHCl3 (3×). The combined organics were washed with 5% aq. NaHCO3, brine, dried (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (EtOAc-hexane, 5:95) affording the title compound. 1H NMR (500 MHz, acetone-d6): δ 7.86 (m, 2H), 7.38 (s, 1H), 7.31-7.26 (m, 3H), 3.76 (s, 3H), 2.39 (s, 3H).

後処理

  1. stirringstirred for 20 min
  2. extractionextracted with CHCl3 (3×)
  3. washThe combined organics were washed with 5% aq. NaHCO3, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-0ad62dc707d349b9a5818c65d98e9a90
出典データセット
uspto-grants-2009_06
特許番号
US07553973B2

反応ノート

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