Hydrogen Bromide → 3-Bromo-4-cyclohexylphenylglyoxylic acid

HRID 444568Notes

Reaction equation

HRID 444568 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.N([O-])=O.[Na+].O.[BrH:26]>>[Br:26][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 4

HCID 260Hydrogen Bromide2×HCID 962WaterHCID 20515218Ethyl 3-amino-4-cyclohexylphenylglyoxylateHCID 23668193Sodium Nitrite

Product 1

HCID 205151793-Bromo-4-cyclohexylphenylglyoxylic acid

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-4c07c34162b943b1898eb6e8b875a953
Source dataset
uspto-grants-1981_04
Patent number
US04264627

Reaction notes

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