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

HRID 517550노트

반응식

HRID 517550 반응식
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

참가 물질

8

반응물 3

HCID 6228DimethylformamideHCID 1110192-Chloropropionyl chlorideHCID 178419771HCID 178419771, 화합물

생성물 1

HCID 867114911-(3-Bromophenyl)-3-chlorobutan-2-one수율 38%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-fc912b58edfe488c8a0dd0b8c298eebc
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115120B2

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