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

HRID 465872

반응식

HRID 465872 반응식
[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

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 115633-BromophenolHCID 144239Dimethylthexylsilyl chloride

생성물 1

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

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8058Hexane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-2120ce38006b45ea849d9d008495a88d
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153327

연결된 노트

불러오는 중…