Methyl iodide → Ethyl 2-(4-bromophenyl)propanoate

HRID 406980노트

반응식

HRID 406980 반응식
[Li+].[CH3:2]C([N-]C(C)C)C.CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C.[Br:29][C:30]1[CH:35]=[CH:34][C:33]([CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:32][CH:31]=1.CI.[NH4+].[Cl-]>C1COCC1>[Br:29][C:30]1[CH:31]=[CH:32][C:33]([CH:36]([CH3:2])[C:37]([O:39][CH2:40][CH3:41])=[O:38])=[CH:34][CH:35]=1

참가 물질

7

반응물 5

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 7020609Ethyl 2-(4-bromophenyl)acetateHCID 22742125Tetrahydrofuran heptane ethylbenzol

생성물 1

HCID 13840376Ethyl 2-(4-bromophenyl)propanoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

2.0 M LDA in heptane/THF/ethylbenzene (6.0 mL, 12 mmol) was slowly added to a solution of ethyl (4-bromophenyl)acetate (2.43 g, 10.0 mmol) in THF (20 mL) at −78° C. and then the mixture was stirred for 30 min. Methyl iodide (0.93 mL, 15 mmol) was added at −78° C. and then the reaction was stirred for an additional 30 min. Saturated NH4Cl aq. was added to quench the reaction. The mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%) to afford the desired product (2.0 g).

후처리

  1. stirringthe reaction was stirred for an additional 30 min
  2. customto quench
  3. customthe reaction
  4. extractionThe mixture was extracted with ethyl acetate
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexane (0-10%)

출처 및 근거

ORD 기록
ord-ea33d576172040488a0aefe9e7e83041
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754114B2

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