2-Bromophenol → HCID 69417921, 화합물

HRID 1373639노트

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HRID 1373639 반응식
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6]S(C)(=O)=O.[Br:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1O.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH3:1][O:2][C:3](=[O:13])[C:4]([CH3:12])([CH3:11])[CH2:5][O:6][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[Br:14]

참가 물질

5

반응물 3

HCID 72442-BromophenolHCID 10796Cesium carbonateHCID 71623346Methyl 2,2-dimethyl-3-((methylsulfonyl)oxy)propanoate

생성물 1

HCID 69417921HCID 69417921, 화합물수율 70%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
100 °C

실험 절차

A first intermediate compound 3-(2-Bromo-phenoxy)-2,2-dimethyl-propionic acid, was produced as follows: To a mixture of 3-methanesulfonyloxy-2,2-dimethyl-propionic acid methyl ester (20.00 g, 95.23 mmol) and 2-bromophenol (16.48 g, 95.23 mmol) in acetonitrile (200 mL) was added Cs2CO3 (46.50 g, 142.80 mmol) and the mixture was heated at 100° C. in a sealed flask overnight. The resulting suspension was filtered. The solvent was evaporated and the crude material was partitioned between dichloromethane (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL), dried over Na2SO4 and evaporation of the solvent gave 3-(2-bromo-phenoxy)-2,2-dimethyl-propionic acid methyl ester (19.00 g, 70%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 7.55 (d, 1H), 7.26–7.22 (m, 1H), 6.87–6.80 (m, 2H), 4.02 (s, 2H), 3.72 (s, 3H), 1.40 (s, 6H).

후처리

  1. filtrationThe resulting suspension was filtered
  2. customThe solvent was evaporated
  3. customthe crude material was partitioned between dichloromethane (100 mL) and water (100 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with dichloromethane (50 mL)
  6. dry with materialdried over Na2SO4 and evaporation of the solvent

출처 및 근거

ORD 기록
ord-13f5cca6f640490b9743dd2d46b7bb3d
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07160888B2

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