Benzoyl Peroxide → 4-(Bromomethyl)-3-chlorobenzoic acid

HRID 7738Notes

Reaction equation

HRID 7738 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[CH3:11])[C:5]([OH:7])=[O:6].[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 788403-Chloro-4-methylbenzoic Acid

Product 1

HCID 219249954-(Bromomethyl)-3-chlorobenzoic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 3-chloro-4-methylbenzoic acid (5.0 g, 29 mmol), N-bromosuccinimide (5.7 g, 32 mmol), benzoyl peroxide (710 mg, 2.9 mmol) in CCl4 (300 mL) was heated at reflux for 2.5 h. The mixture was concentrated under reduced pressure and dissolved in MTBE. The organic mixture was washed with 1N NaOH (3×25 mL). The aqueous mixture was acidified with 1N HCl to pH 2 and extracted with CH2Cl2 (3×25 mL). The combined organic layers were dried over MgSO4, filtered and concentrated to afford 4-(bromomethyl)-3-chlorobenzoic acid.

Workup

  1. temperatureat reflux for 2.5 h
  2. concentrationThe mixture was concentrated under reduced pressure
  3. dissolutiondissolved in MTBE
  4. washThe organic mixture was washed with 1N NaOH (3×25 mL)
  5. extractionextracted with CH2Cl2 (3×25 mL)
  6. dry with materialThe combined organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-4ebe673163ca41e2bbd2f1f42373a799
Source dataset
uspto-grants-2006_08
Patent number
US07087601B2

Reaction notes

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