Hydrogen Bromide → 3-Bromo-4-cyclohexylphenylglyoxylic acid

HRID 236826Notes

Reaction equation

HRID 236826 reaction equation
N[C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([O:17]CC)=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[BrH:21].N([O-])=O.[Na+]>O>[Br:21][C:2]1[CH:3]=[C:4]([C:14](=[O:20])[C:15]([OH:17])=[O:16])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 20515218Ethyl 3-amino-4-cyclohexylphenylglyoxylateHCID 23668193Sodium Nitrite

Product 1

HCID 205151793-Bromo-4-cyclohexylphenylglyoxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 11.1 g. (0.044 moles) of ethyl 3-amino-4-cyclohexylphenylglyoxylate suspension in 225 ml. of 40% hydrobromic acid and cooled to 0° C. is added dropwise a solution of 2.34 g. of sodium nitrite in 30 ml. of water. To this mixture is added a solution of 20 g. of cuprous bromide in 350 ml. of 40% hydrobromic acid added portion wise and stirred for 15 hours. The reaction mixture is then poured onto ice water, extracted with chloroform, dried over sodium sulfate and concentrated in vacuo. The residue is then crystallized to obtain 3-bromo-4-cyclohexylphenylglyoxylic acid.

Workup

  1. additionis added dropwise a solution of 2.34 g
  2. additionTo this mixture is added a solution of 20 g
  3. additionThe reaction mixture is then poured onto ice water
  4. extractionextracted with chloroform
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is then crystallized

Sources & evidence

ORD record
ord-d7f662449d6341699710d00bed4f87e8
Source dataset
uspto-grants-1979_06
Patent number
US04157449

Reaction notes

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