4-Bromo-1,2-dichlorobenzene → 1-(3,4-Dichlorophenyl)-2-methoxyethanone

HRID 2279501

반응식

HRID 2279501 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([Cl:9])[CH:3]=1.[Li]CCCC.CON(C)[C:18](=[O:22])[CH2:19][O:20][CH3:21]>CCOCC>[Cl:9][C:4]1[CH:3]=[C:2]([C:18](=[O:22])[CH2:19][O:20][CH3:21])[CH:7]=[CH:6][C:5]=1[Cl:8]

참가 물질

5

반응물 3

HCID 290134-Bromo-1,2-dichlorobenzeneHCID 14872187N,2-dimethoxy-N-methylacetamideHCID 178418339Butyllithium

생성물 1

HCID 202556411-(3,4-Dichlorophenyl)-2-methoxyethanone수율 79%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

To a solution of 4-bromo-1,2-dichlorobenzene (2.04 g, 9.01 mmol) and ether (5 mL) cooled to −78° C. was added as a steady stream n-BuLi (3.61 ml, 9.01 mmol) and the reaction was stirred for 10 min then cannulated into a solution of N,2-dimethoxy-N-methylacetamide (1.0 g, 7.51 mmol) and ether (10 mL) which was stirred for an additional 20 min. The reaction was quenched with water and extracted with EtOAc. The organic fractions were dried, filtered and concentrated. The crude product which was purified by SiO2 chromatography eluting with hexane/EtOAc (9:1) to afford 1.30 g (79.0%) of 1-(3,4-dichlorophenyl)-2-methoxyethanone as a white solid (192).

후처리

  1. stirringwas stirred for an additional 20 min
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc
  4. customThe organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product which was purified by SiO2 chromatography
  8. washeluting with hexane/EtOAc (9:1)

출처 및 근거

ORD 기록
ord-659f627637a14cbf883628fb6637c826
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133187B2

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