Dimethylformamide → 3-(Benzyloxy)-4-bromophenol

HRID 26084

反応式

HRID 26084 の反応式
[H-].[K+].CN(C)C=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][C:10]=1[OH:16].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.O>[CH2:17]([O:16][C:10]1[CH:11]=[C:12]([OH:13])[CH:14]=[CH:15][C:9]=1[Br:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 811054-BromoresorcinolHCID 82127Potassium hydride

生成物 1

HCID 156706543-(Benzyloxy)-4-bromophenol

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

反応条件

温度
0 °C

実験手順

To a 0° C. slurry of 1.7 g. (42.5 mmoles) of potassium hydride in 35 ml. of N,N-dimethylformamide is slowly added a solution of 7.22 g. (38.2 mmoles) of 4-bromoresorcinol. The resultant mixture is stirred for 30 minutes and then 4.54 ml. (38.2 mmoles) of benzyl bromide is slowly added. The reaction mixture is stirred 3 hours longer at 0° C. and then added to 200 ml. of cold water and 200 ml. of ether. The ether extract is washed twice with 200 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The crude oil is purified via column chromatography on 400 g. of silica gel eluted with 25% ether-pentane to yield (in order of elution) 2.2 g. (16%) of 2,4-dibenzyloxybromobenzene, 0.21 g. (2%) of 5-benzyloxy-2-bromophenol and 3.52 g. (33%) of 3-benzyloxy-4-bromophenol.

後処理

  1. customTo a 0° C.
  2. additionadded to 200 ml
  3. extractionThe ether extract
  4. washis washed twice with 200 ml
  5. dry with materialportions of water, dried over magnesium sulfate
  6. customevaporated to an oil
  7. customThe crude oil is purified via column chromatography on 400 g
  8. washof silica gel eluted with 25% ether-pentane
  9. customto yield
  10. wash(in order of elution) 2.2 g

出典と根拠

ORDレコード
ord-cbaf3fd342894c14a78febb86ca2b7a8
出典データセット
uspto-grants-1979_04
特許番号
US04147872

関連ノート

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