Benzoyl Peroxide → 4-(Bromomethyl)benzoic acid

HRID 430364Notes

Reaction equation

HRID 430364 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>C1C=CC=CC=1>[Br:29][CH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl Peroxide2×HCID 7470P-Toluic AcidHCID 67184N-bromobutanimide

Product 1

HCID 225994-(Bromomethyl)benzoic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 4-methyl-benzoic acid (10 g, 73.4 mmol) in benzene (133 mL) was treated with benzoyl peroxide (72 mg, 0.29 mmol). This mixture was heated to reflux until it became homogeneous. At this time, the reaction was treated with N-bromosuccinimide (13 g, 73.4 mmol) and additional benzoyl peroxide (72 mg, 0.29 mmol). This mixture was heated at reflux for 2.5 h. At this time, the reaction was cooled to 25° C. The resulting precipitate was collected by filtration and washed with hot water (50 mL). The solid was taken up in water (150 mL). This slurry was heated at 80° C. and then filtered while hot. The solid that was collected was dried in vacuo to afford 4-bromomethyl-benzoic acid (12.3, 77.9%) as a white solid: mp 224-226° C.; EI-HRMS m/e calcd for C8H7BrO2 (M+) 213.9629, found 213.9628.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux until it
  3. temperatureThis mixture was heated
  4. temperatureat reflux for 2.5 h
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with hot water (50 mL)
  7. temperatureThis slurry was heated at 80° C.
  8. filtrationfiltered while hot
  9. customThe solid that was collected
  10. customwas dried in vacuo

Sources & evidence

ORD record
ord-23933e8fc55b402bb77d850c29d45680
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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