Hydrochloric Acid → 1-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene

HRID 662050

反応式

HRID 662050 の反応式
[CH3:1][C:2]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])[CH3:3].CCN(CC)CC.[Br:16][C:17]1[CH:18]=[C:19]([CH2:23][OH:24])[CH:20]=[CH:21][CH:22]=1.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[Br:16][C:17]1[CH:18]=[C:19]([CH2:23][O:24][Si:5]([C:2]([CH3:4])([CH3:3])[CH3:1])([CH3:7])[CH3:6])[CH:20]=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 851413-Bromobenzyl alcohol2 回

生成物 1

HCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzene収率 95.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

TBSCl (18.7 g, 124.3 mmol), Et3N (14.08 g, 139.2 mmol) and DMAP (194.3 mg, 8.9 mmol) were dissolved in CH2Cl2 (120 mL) and the solution was cooled to 0-5° C. (3-Bromophenyl)methanol (18.5 g, 99.4 mmol) was added dropwise to the solution. After the addition of the (3-Bromophenyl)methanol, the mixture was warmed to room temperature and stirred for 2 h. 5% HCl was added to the reaction mixture to adjust the pH=4-5. Then the organic phase was separated and the aqueous layer was extracted with CH2Cl2 (50 mL×2). The combined organic phases were washed with water and dried over Na2SO4. After removing the solvent, 28.5 g of {[(3-bromophenyl)methyl]oxy}(1,1-dimethylethyl)dimethylsilane was obtained (Yield: 95.1%).

後処理

  1. additionwas added dropwise to the solution
  2. customThen the organic phase was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL×2)
  4. washThe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customAfter removing the solvent

出典と根拠

ORDレコード
ord-1cbda912a6a740f29e66b89a6bc5dd98
出典データセット
uspto-grants-2011_12
特許番号
US08084449B2

関連ノート

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