4-Bromophenol → 4-(1,1-Dimethyl-2-propynyloxy)bromobenzene

HRID 1073931ノート

反応式

HRID 1073931 の反応式
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.[CH3:9][C:10](O)([C:12]#[CH:13])[CH3:11].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH3:9][C:10]([CH3:11])([O:7][C:6]1[CH:5]=[CH:4][C:3]([Br:8])=[CH:2][CH:1]=1)[C:12]#[CH:13]

参加物

6

反応物 4

HCID 78084-BromophenolHCID 82582-Methyl-3-butyn-2-olHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 540101944-(1,1-Dimethyl-2-propynyloxy)bromobenzene収率 15.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

69.2 g of p-bromophenol and 33.6 g of 2-methylbut-3-yn-2-ol were dissolved in 600 ml of dichloromethane and 75 ml of diethyl azodicarboxylate were added. 126 g of triphenylphosphine were added portionwise and the mixture was stirred overnight. The mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution, dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:10) for the elution. There was obtained an oil which was distilled to give 14.4 g of 4-(1,1-dimethyl-2-propynyloxy)bromobenzene of boiling point 96°-106° C./1 mmHg.

後処理

  1. washThe mixture was washed with dilute hydrochloric acid and 2M sodium hydroxide solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated
  4. customThe residue was chromatographed on silica gel
  5. washfor the elution
  6. customThere was obtained an oil which
  7. distillationwas distilled

出典と根拠

ORDレコード
ord-c8ae302e66e9466182d94de4e4e16313
出典データセット
uspto-grants-1990_11
特許番号
US04971982

反応ノート

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