Sodium hydride → Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate

HRID 273380

반응식

HRID 273380 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[H-].[Na+].[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20]Br>CN(C)C=O.C(OCC)(=O)C>[Br:16][C:17]1[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=1)[CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 79706Benzenepropanoic acid, 4-hydroxy-, methyl ester

생성물 1

HCID 23136270Methyl 4-[(3-bromophenyl)methoxy]benzenepropanoate수율 144%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of methyl 3-(4-hydroxyphenyl)propanoate (0.3 g, 1.67 mmol) in N,N-dimethylformamide (4.0 mL) was added 60% sodium hydride (0.073 g, 1.83 mmol) at 0° C. with stirring, and the mixture was stirred at the same temperature for 15 min. Then, 3-bromobenzylbromide (0.44 g, 1.75 mmol) was added to the mixture at 0° C. with stirring, and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was diluted with ethyl acetate and washed with 5% aqueous potassium hydrogensulfate solution and saturated brine. The ethyl acetate layer was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (0.84 g, yield 72%) as a colorless powder.

후처리

  1. stirringthe mixture was stirred at the same temperature for 15 min
  2. stirringwith stirring
  3. stirringthe mixture was stirred at room temperature for 2 hrs
  4. washwashed with 5% aqueous potassium hydrogensulfate solution and saturated brine
  5. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1121fc2544844b9485373f654fe62713
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456218B2

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