2-Bromophenol → HCID 69417921、化合物

HRID 1373639ノート

反応式

HRID 1373639 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 69417921HCID 69417921、化合物収率 70%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-13f5cca6f640490b9743dd2d46b7bb3d
出典データセット
uspto-grants-2007_01
特許番号
US07160888B2

反応ノート

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