O-Cresol → 1-(2-Bromoethoxy)-2-methylbenzene

HRID 271228노트

반응식

HRID 271228 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].[Br:11][CH:12](Br)[CH3:13].S([O-])(O)(=O)=O.C([NH3+])(C)(C)C>>[Br:11][CH2:12][CH2:13][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1]

참가 물질

5

반응물 4

HCID 335O-CresolHCID 112011,1-DibromoethaneHCID 14798Sodium Hydroxide2회HCID 24996679t-Butylammonium hydrogen sulfate

생성물 1

HCID 16225721-(2-Bromoethoxy)-2-methylbenzene

실험 절차

2-Methyl-phenol (1 g, 9.25 mmol) in NaOH (aq) (3.24 mL, 12.96 mmol, 4M soln.) was treated with dibromoethane (2.74 mL, 31.7 mmol) and t-butylammoniumhydrogen sulfate (catalytic), and then placed in a Robbins™ oven at 99° C. for 72 hours. The pH was then adjusted to ˜8 with NaOH (4M aq. soln.) and the product extracted with CH2Cl2 (x3). The combined organic layer was washed with H2O (x2) and brine, dried over MgSO4. The resulting oil taken up in 4:1 hexane/EtOAc and passed through a plug of silica gel. The plug was then washed with 4:1 hexane/EtOAc and the filtrate concentrated to provide crude 2-bromo-1-(2-methylphenoxy)ethane.

후처리

  1. extractionthe product extracted with CH2Cl2 (x3)
  2. washThe combined organic layer was washed with H2O (x2) and brine
  3. dry with materialdried over MgSO4
  4. washThe plug was then washed with 4:1 hexane/EtOAc
  5. concentrationthe filtrate concentrated

출처 및 근거

ORD 기록
ord-21e6a719f0544b869f90d556cdfe0898
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452889B2

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