Hydrochloric Acid → 2-Bromo-1-(2-ethylphenyl)ethan-1-one

HRID 914721

반응식

HRID 914721 반응식
[Br:1][CH:2](Br)C.[Li+].CC([N-]C(C)C)C.CO[C:15](=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH3:23].C([Li])CCC.Cl>C1COCC1.CCCCCC>[Br:1][CH2:2][C:15]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22][CH3:23])=[O:24]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 112011,1-DibromoethaneHCID 583295Methyl 2-ethylbenzoateHCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

생성물 1

HCID 234426012-Bromo-1-(2-ethylphenyl)ethan-1-one수율 41.8%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매

실험 절차

To a solution of 15.2 g (88 mmol) dibromethane in 120 ml THF at −75° C. was added 44 ml (88 mmol) of a 2M solution of LDA in THF and subsequently 6.57 g (40 mmol) ethyl-benzoic acid methyl ester in 80 ml THF. 37.5 ml of a 1.6 M n-butyl lithium solution in n-hexane was added and after 30 min the mixture was treated carefully below −65° C. with 35 ml HCl (37%). The mixture was washed with water and NaHCO3 aq. and the organic phase was dried with MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica eluting with ethyl acetate/hexane 1:9 twice to afford 3.8 g (41%) of the title compound as yellow oil. MS (m/e): 227.1 (M+H, 100%).

후처리

  1. washThe mixture was washed with water and NaHCO3 aq.
  2. dry with materialthe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica eluting with ethyl acetate/hexane 1:9 twice

출처 및 근거

ORD 기록
ord-7e867a48daa64a2898efc634d62c6431
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265109B2

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