2,4-Difluorophenol → (S)-benzyl 4-(2,4-difluorophenoxy)-3-oxobutan-2-ylcarbamate

HRID 1098988노트

반응식

HRID 1098988 반응식
Br[CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[OH:26].[F-].[K+]>CN(C=O)C.ClCCl.O>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[O:26][CH2:2][C:3](=[O:17])[C@@H:4]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:5]

참가 물질

7

반응물 3

HCID 1230512,4-DifluorophenolHCID 522689Potassium FluorideHCID 15485144(S)-benzyl 4-bromo-3-oxobutan-2-ylcarbamate

생성물 1

HCID 59339874(S)-benzyl 4-(2,4-difluorophenoxy)-3-oxobutan-2-ylcarbamate수율 94.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매2회

실험 절차

A mixture of (S)-benzyl 4-bromo-3-oxobutan-2-ylcarbamate (prepared according to R. V. Hoffman et al., J. Org. Chem. 2001, 66, 5790-5795) (600 mg, 2.00 mmol), 2,4-difluorophenol (312 mg, 2.40 mmol) and potassium fluoride (380 mg, 6.54 mmol) in DMF (4 mL) was stirred at r.t. for 17 h. Water (15 mL) and dichloromethane (3 mL) were added and the mixture was stirred for 30 min. The mixture was added to a phase separator. The water phase was once more stirred with dichloromethane (3 mL), and added to the phase separator. The organic phases were concentrated and the residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1) to give the title compound as a white solid (658 mg, 94% yield).

후처리

  1. stirringthe mixture was stirred for 30 min
  2. additionThe mixture was added to a phase separator
  3. additionadded to the phase separator
  4. concentrationThe organic phases were concentrated
  5. customthe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 3/1)

출처 및 근거

ORD 기록
ord-9db79ff1d7424dd585781c09e1e73fed
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143290B2

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