Carbon Tetrachloride → HCID 69694189, compound

HRID 896018Notes

Reaction equation

HRID 896018 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH3:19].[Br:21]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCOCC>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:19][Br:21]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide2×HCID 69693963HCID 69693963, compound

Product 1

HCID 69694189HCID 69694189, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 4-(4-Methoxy-phenoxy)-2-methyl-benzoic acid methyl ester (2.8 grams, 10.3 mmol), N-bromosuccinimide (2.14 grams, 12 mmol) and carbon tetrachloride (12 mL) was added a crystal of benzoyl peroxide. The mixture was heated to reflux for 2 hours, and an additional 2.1 grams of N-bromosuccinimide was added. After refluxing for an additional 4 hours, the mixture was cooled to room temperature, diluted with ether, and the organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated, affording 3 grams of 2-Bromomethyl-4-(4-methoxy-phenoxy)-benzoic acid methyl ester as a colorless oil. 1H NMR (CDCl3, 500 MHz): δ 7.96 (d, 1H, J=8.8 Hz), 7.05-6.90 (m, 6H), 6.87 (dd, 1H, J=2.6, 8.3 Hz), 4.92 (s, 2H), 3.93 (s, 3H), 3.85(s, 3H) ppm.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 hours
  3. temperatureAfter refluxing for an additional 4 hours
  4. washthe organic phase was washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-42e9b73d05a64074ba456dbb60df9a3b
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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