Imidazole → Phenol, 4-(4-bromobutyl)-

HRID 1586317노트

반응식

HRID 1586317 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32]O)=[CH:25][CH:24]=1.N1C=CN=C1>C(Cl)Cl>[OH:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][CH2:31][CH2:32][Br:20])=[CH:25][CH:24]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 133925134-(4-Hydroxybutyl)phenol

생성물 1

HCID 11128076Phenol, 4-(4-bromobutyl)-수율 88%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A solution of triphenylphosphine (144.1 mmole, 37.80 g) in methylene chloride (556 ml) was treated with bromine (144.1 mmole, 23.03 g) until a pale yellow color persisted. After stirring approximately 15 minutes, a solution of 4-(4-hydroxyphenyl)butanol (96.1 mmole, 15.97 g) and imidazole (192.2 mmole, 13.08 g) in methylene chloride (355 ml) was added over a 15 minute period. Approximately 4 hours later, the reaction suspension was filtered and the filtrate was reduced in volume. To the reduced filtrate was added silica gel and the suspension was reduced to dryness. This material was filtered and the first six fractions were eluted with 10% ethyl acetate:hexane. Fractions 7 through 12 were eluted with 20% ethyl acetate:hexane. Fractions 7 through 10 were combined, reduced in volume, dried over sodium sulfate, filtered and concentrated in vacuo to afford 19.32 g (88%) of the title compound as an oil.

후처리

  1. filtrationApproximately 4 hours later, the reaction suspension was filtered
  2. additionTo the reduced filtrate was added silica gel
  3. filtrationThis material was filtered
  4. washthe first six fractions were eluted with 10% ethyl acetate
  5. washFractions 7 through 12 were eluted with 20% ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-77848eb60cab45e4bf3de75dab0e171a
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942530

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