Water → 4-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene

HRID 2219195노트

반응식

HRID 2219195 반응식
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([CH3:15])[CH:9]=1.[CH3:16][O:17][CH:18]([O:21][CH3:22])[CH2:19]Br.O>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:19][CH:18]([O:21][CH3:22])[O:17][CH3:16])=[C:10]([CH3:15])[CH:9]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 168964-Bromo-2-methylphenolHCID 816722-Bromo-1,1-dimethoxyethane

생성물 1

HCID 196085464-Bromo-1-[(2,2-dimethoxyethyl)oxy]-2-methylbenzene수율 40%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Powdered potassium carbonate (3.36 g, 24.3 mmol) is added to a stirred solution of 4-bromo-2-methylphenol (3.03 g, 16.2 mmol) and bromoacetaldehyde dimethyl acetal (3.56 g, 21.1 mmol) in anhydrous DMF (20 mL). The resultant mixture is stirred at 85° C. under nitrogen for 24 hours. The mixture is cooled to ambient temperature; then water (100 mL) and EtOAc (100 mL) are added to the mixture. The organic layer is separated, dried over MgSO4, filtered and concentrated. The oil is chromatographed on silica (gradient 5-20% EtOAc in hexane) to give 1.78 g (6.47 mmol, 40% yield) of the title compound. EIMS: m/z 274 (M+, 79Br), 276 (M+, 81Br). Analysis for C11H15BrO3: calcd: C, 48.02; H, 5.50; found: C, 48.32; H, 5.53.

후처리

  1. customThe organic layer is separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe oil is chromatographed on silica (gradient 5-20% EtOAc in hexane)

출처 및 근거

ORD 기록
ord-00d182b0994e451891300ff26f6dcaa6
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07414063B2

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