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

HRID 1915479

반응식

HRID 1915479 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-664d4f9dd909433ea7b5b0a8b154439f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614327B2

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