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

HRID 1915479

反応式

HRID 1915479 の反応式
[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

参加物

6

反応物 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 8396o-Cyclohexylphenol

生成物 1

HCID 221345164-Bromo-2-cyclohexyl-phenol収率 93%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒2 回HCID 962Water溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-664d4f9dd909433ea7b5b0a8b154439f
出典データセット
uspto-grants-2013_12
特許番号
US08614327B2

関連ノート

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