4-Bromobenzaldehyde → HCID 5151110、化合物

HRID 1586236ノート

反応式

HRID 1586236 の反応式
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.C1(P(=[CH:29][CH:30]=[O:31])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:29][CH:30]=[O:31])=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 707414-BromobenzaldehydeHCID 75051(Triphenylphosphoranylidene)acetaldehyde

生成物 1

HCID 5151110HCID 5151110、化合物収率 35.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Part A. 4-bromobenzaldehyde (9.11 gm, 49.28 mmol) and (triphenylphosphoranylidene) acetaldehyde (15.00 gm, 49.28 mmol) were combined in 250 mL of methylene chloride and stirred overnight at room temperature. The volatiles were removed under vacuum and the residue dissolved in 200 mL of EtOAc, filtered through a pad of silica gel and concentrated to dryness. The resulting residue was purified by flash chromatography on silica gel eluting hexane:ethyl acetate (3:1, v:v) to give 3-(4-bromophenyl) acrolein as a pale yellow solid 3.67 gm, (35%). MS m/e 211 (M+H)+ 1 H NMR (CDCl3) 6.70 (dd, 1H), 7.43 (m, 3H), 7.54 (d, 2H), 9.69 (d, 1H).

後処理

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe residue dissolved in 200 mL of EtOAc
  3. filtrationfiltered through a pad of silica gel
  4. concentrationconcentrated to dryness
  5. customThe resulting residue was purified by flash chromatography on silica gel
  6. washeluting hexane:ethyl acetate (3:1, v:v)

出典と根拠

ORDレコード
ord-5262caeffb054c2ca1be9aa1380f6067
出典データセット
uspto-grants-1999_08
特許番号
US05942544

反応ノート

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