3-Chlorophenylacetic acid → HCID 22626651, compound

HRID 449780Notes

Reaction equation

HRID 449780 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:19][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 158793-Chlorophenylacetic acidHCID 67184N-bromobutanimide

Product 1

HCID 22626651HCID 22626651, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

3-Chlorophenylacetic acid (20.90 g, 122.51 mmol) and NBS (23.50 g, 132.03 mmol) were dissolved in carbon tetrachloride (300 mL), then BPO (300 mg) was added, the resulting reaction was heated to reflux under a sunlamp for 5 hours, then cooled to room temperature, filtered and concentrated to give the desired α-bromo-3-chlorophenylacetic acid. 1.40 g of this α-bromo-3-chlorophenylacetic acid was reacted with 3,4-dimethylphenol (686 mg) according to the General procedure C to give 1.47 g of the desired title compound. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ ppm 2.17 (s, 3 H) 2.21 (s, 3 H) 5.58 (s, 1 H) 6.65 (dd, J=8.20, 2.64 Hz, 1 H) 6.78 (d, J=2.64 Hz, 1 H) 7.01 (d, J=8.20 Hz, 1 H) 7.29-7.40 (m, 2 H) 7.42-7.52 (m, 1 H) 7.59 (s, 1 H).

Workup

  1. additionBPO (300 mg) was added
  2. customthe resulting reaction
  3. temperaturewas heated
  4. temperatureto reflux under a sunlamp for 5 hours
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-91140a1c438b4fd38f22a59b9ebdcc0e
Source dataset
uspto-grants-2013_07
Patent number
US08486918B2

Reaction notes

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