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Potassium Carbonate → Tert-butyl (2-bromo-4-fluorophenoxy)acetate

HRID 2250883
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HRID 2250883 반응식
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C>[C:21]([O:20][C:18](=[O:19])[CH2:17][O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])([CH3:24])([CH3:23])[CH3:22]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 6054722-Bromo-4-fluorophenol

생성물 1

HCID 59642165Tert-butyl (2-bromo-4-fluorophenoxy)acetate수율 83.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-bromo-4-fluorophenol (2.15 g, 11.25 mmol) in DMF (60 ml) was treated with potassium carbonate (7.77 g, 96.25 mmol) and t-butyl bromoacetate (1.99 ml, 13.5 mmol) at 60° C. for 12 hours. The reaction mixture was filtered through celite, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude was absorbed on silica and purified on a silica gel column with a 5%-10% ethyl acetate/hexanes gradient to give the product as colorless oil (2.86 g, 83%).

후처리

  1. filtrationThe reaction mixture was filtered through celite
  2. custompartitioned between water and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude was absorbed on silica
  8. custompurified on a silica gel column with a 5%-10% ethyl acetate/hexanes gradient

출처 및 근거

ORD 기록
ord-e92ad4b865844adf8dd12b496ea9ad95
출처 데이터셋
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07317125B2

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