3-Chlorophenylacetic acid → HCID 22626651, compound

HRID 449782Notes

Reaction equation

HRID 449782 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, 122.52 mmol) and NBS (23.50 g, 133.14 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. 5.00 g of this acid was then reacted with 3,4-dimethyl benzenethiol (2.85 g, 20.62 mmol) and sodium hydride (60% oil dispersion, 4.50 g, 87.50 mmol) to yield Intermediate 3, which was used in the next synthetic step without further purification.

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-0a6289b155ab4731bc9f143f0641fe37
Source dataset
uspto-grants-2013_07
Patent number
US08486918B2

Reaction notes

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