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

HRID 2090132

反応式

HRID 2090132 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-cbd7c1116b21420aa37a89678e0f5b8b
出典データセット
uspto-grants-2013_05
特許番号
US08436133B2

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