3,4-Dimethylphenol → HCID 67774087, compound

HRID 449781Notes

Reaction equation

Br[CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[CH:7]=1)[C:3]([OH:5])=[O:4].[CH3:13][C:14]1[CH:15]=[C:16]([OH:21])[CH:17]=[CH:18][C:19]=1[CH3:20]>>[Cl:12][C:8]1[CH:7]=[C:6]([CH:2]([O:21][C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[C:14]([CH3:13])[CH:15]=2)[C:3]([OH:5])=[O:4])[CH:11]=[CH:10][CH:9]=1

Participants

Reactant 2

HCID 72493,4-Dimethylphenol

HCID 22626651HCID 22626651, compound

Product 1

HCID 67774087HCID 67774087, compoundYield 90.1%

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).

Sources & evidence

ORD record: ord-be56ee665a6b4e1f93808270a2b2c49d
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486918B2

Reaction notes

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