Dimethylformamide → 1-(3-Bromophenyl)-3-chlorobutan-2-one

HRID 517550ノート

反応式

HRID 517550 の反応式
CN(C=O)C.[Br-].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][Zn+].[Cl:16][CH:17]([CH3:21])[C:18](Cl)=[O:19]>C1(C)C=CC=CC=1.CCCCCC.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:7][C:8]1[CH:9]=[C:10]([CH2:11][C:18](=[O:19])[CH:17]([Cl:16])[CH3:21])[CH:13]=[CH:14][CH:15]=1

参加物

8

反応物 3

HCID 6228DimethylformamideHCID 1110192-Chloropropionyl chlorideHCID 178419771HCID 178419771、化合物

生成物 1

HCID 867114911-(3-Bromophenyl)-3-chlorobutan-2-one収率 38%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of CuCN(LiCl)2 (2.5 mL, 2.500 mmol), DMF (0.194 mL, 2.5 mmol) and (3-bromobenzyl)zinc(II) bromide (5 mL, 2.5 mmol) was stirred at RT for 20 min. A solution of 2-chloropropanoyl chloride (0.244 mL, 2.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.087 g, 0.075 mmol) in toluene (5 mL) was added to the reaction mixture. After 45 min the reaction was diluted with hexane and EtOAc and solid silica gel was added. The mixture was stirred for 5 min and the solid was filtered. The organic layer was concentrated, and loaded to silica gel column chromatography for purification (0-30% EtOAc/Hexane) to afford a colorless liquid (246 mg, 38%). MS (ES+) C10H10BrClO requires: 260, 262, found: 261 263 [M+H]+(1:1).

後処理

  1. additionwas added
  2. stirringThe mixture was stirred for 5 min
  3. filtrationthe solid was filtered
  4. concentrationThe organic layer was concentrated
  5. customloaded to silica gel column chromatography for purification (0-30% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-fc912b58edfe488c8a0dd0b8c298eebc
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

反応ノート

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