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

HRID 1276525노트

반응식

HRID 1276525 반응식
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

참가 물질

6

반응물 3

HCID 79271,3-DibromobenzeneHCID 14496CyclobutanoneHCID 178418339Butyllithium

생성물 1

HCID 184615711-(3-Bromophenyl)-cyclobutanol수율 66.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b433bcd288e5428f95e3795ff0d70b0f
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166064

반응 노트

불러오는 중…