Hydrogen Bromide → 4-Bromo-2-cyclohexyl-phenol

HRID 2404877

반응식

HRID 2404877 반응식
[CH:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:14].CS(C)=O>C(O)(=O)C.O>[Br:14][C:11]1[CH:10]=[CH:9][C:8]([OH:13])=[C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH:12]=1

참가 물질

6

반응물 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 8396o-Cyclohexylphenol

생성물 1

HCID 221345164-Bromo-2-cyclohexyl-phenol수율 93%

시약·촉매·용매 2

HCID 176Acetic Acid용매2회HCID 962Water용매

실험 절차

To a stirring solution of 2-cyclohexylphenol (26.0 g, 146.8 mmol) in glacial acetic acid (100 mL) was added HBr in acetic acid (150 mL of 33% w/w,) and H2O (52 mL), followed by the dropwise addition of DMSO (100 mL) over 10 min. The reaction was then carefully quenched with saturated NaHCO3 and concentrated in vacuo. The residue was brought up in ether (400 mL), washed with water (2×100 mL) and brine (1×100 mL), and dried over anhydrous Na2SO4, filtered and concentration to yield a crude oil that was purified by silica gel column chromatography, using 15-30% EtOAc/hexane gradient to yield 4-bromo-2-cyclohexyl-phenol (35.0 g, 93%)

후처리

  1. customThe reaction was then carefully quenched with saturated NaHCO3
  2. concentrationconcentrated in vacuo
  3. washwashed with water (2×100 mL) and brine (1×100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentration
  7. customto yield a crude oil that
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9a5ac49ca563407fbf7fa9ac68ba84e4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802700B2

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