Triethylamine → 3-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromide

HRID 465872

反応式

HRID 465872 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.[CH3:16][Si:17](Cl)([CH3:24])[C:18]([CH:21]([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCCCCC>[Br-:1].[CH3:16][Si:17]([CH3:24])([C:18]([CH3:20])([CH3:19])[CH:21]([CH3:23])[CH3:22])[O:8][C:4]1[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=1

参加物

7

反応物 3

HCID 8471TriethylamineHCID 115633-BromophenolHCID 144239Dimethylthexylsilyl chloride

生成物 1

HCID 198754073-[[Dimethyl(1,1,2-trimethylpropyl)silyl]oxy]benzene bromide収率 94.8%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒HCID 8058Hexane溶媒

実験手順

To a stirred solution of 3-bromophenyl alcohol (5.0 g, 26.7 mmol) and triethylamine (3.25 g, 32.1 mmol) in anhydrous CH2Cl2 (125 mL) at room temperature under argon was added dropwise dimethylthexylsilylchloride (5.26 g, 29.4 mmol). After 1.5 hours, 4-dimethylaminopyridine (0.50 g) was added and the stirring was continued for an additional 3 hours. The reaction mixture was diluted with hexane (200 mL) and the precipitate was filtered off. The filtrate was concentrated, partitioned between hexane (200 mL) and 1N aqueous HCl (3×40 mL), and the organic layer was washed with saturated aqueous NaHCO3 (2×40 mL). The organic layer was dried (MgSO4), filtered and concentrated to yield title bromide (8.01 g, 91%).

後処理

  1. waitthe stirring was continued for an additional 3 hours
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. custompartitioned between hexane (200 mL) and 1N aqueous HCl (3×40 mL)
  5. washthe organic layer was washed with saturated aqueous NaHCO3 (2×40 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-2120ce38006b45ea849d9d008495a88d
出典データセット
uspto-grants-1992_10
特許番号
US05153327

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