1,3-Dibromobenzene → 1-(3-Bromophenyl)-cyclobutanol

HRID 2303578ノート

反応式

HRID 2303578 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[CH:3]=1.C([Li])CCC.[C:14]1(=[O:18])[CH2:17][CH2:16][CH2:15]1>O1CCCC1.CCCCCC>[Br:8][C:4]1[CH:3]=[C:2]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)[CH:7]=[CH:6][CH:5]=1

参加物

6

反応物 3

HCID 79271,3-DibromobenzeneHCID 14496CyclobutanoneHCID 178418339Butyllithium

生成物 1

HCID 184615711-(3-Bromophenyl)-cyclobutanol収率 66.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a solution of 1,3-dibromo-benzene (2.36 grams, 10 mmol) in tetrahydrofuran at −78° C. was added a 1.6M solution of n-butyllithium (6.3 ml, 10 mmol) in hexane and stirred for 4 hours. Cyclobutanone (700 mg, 10 mmol) was then added in one portion. After stirring for 2 hours at −78° C., the reaction was quenched with 2N hydrochloric acid. The reaction was warmed to room temperature, diluted with water and extracted with ethyl acetate. The ethyl acetate layer was dried and evaporated to give 2.5 grams of crude product which was purified on silica gel eluting with 50% methylene chloride in hexane to give 1.5 grams of the titled compound.

後処理

  1. stirringAfter stirring for 2 hours at −78° C.
  2. customthe reaction was quenched with 2N hydrochloric acid
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe ethyl acetate layer was dried
  6. customevaporated
  7. customto give 2.5 grams of crude product which
  8. customwas purified on silica gel eluting with 50% methylene chloride in hexane

出典と根拠

ORDレコード
ord-262eb6f471cd4b718da5b06097c52153
出典データセット
uspto-grants-2002_08
特許番号
US06433009B1

反応ノート

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