Dimethylformamide → (4-Bromo-3-methoxy-2naphtyl)-triphenylsilane

HRID 2090132

반응식

HRID 2090132 반응식
[CH3:1][O:2][C:3]1[C:4]([Si:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[Br:32]N1C(=O)CCC1=O.CN(C)C=O.CCOC(C)=O>O>[Br:32][C:12]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Si:13]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:3]=1[O:2][CH3:1]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 42290602-Methoxy-3-(triphenylsilyl)naphthalene

생성물 1

HCID 86653240(4-Bromo-3-methoxy-2naphtyl)-triphenylsilane수율 96%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 150 mL Schlenk flask was charged with 4.68 g of (3-methoxy-2-naphthyl)(triphenyl)silane (11.23 mmol) and 2.20 g of N-Bromosuccinimide (NBS) (12.36 mmol) under argon followed by addition of 10 mL of dimethylformamide (DMF). The resultant mixture was stirred overnight at room temperature, then diluted with 500 mL of water and extracted with 3 times 50 mL of CH2Cl2. The combined organic extracts were washed with 200 mL of water, brine and dried over Na2SO4. The product was purified by passing through short column (silica) using a mixture heptane:EtOAc in a ratio of 15:1 as eluent to afford 5.28 g of product as off-white solid (10.66 mmol) with a yield of 96%.

후처리

  1. extractionextracted with 3 times 50 mL of CH2Cl2
  2. washThe combined organic extracts were washed with 200 mL of water, brine
  3. dry with materialdried over Na2SO4
  4. customThe product was purified

출처 및 근거

ORD 기록
ord-cbd7c1116b21420aa37a89678e0f5b8b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08436133B2

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