Benzoyl Peroxide → 4-(Bromomethyl)benzoic acid

HRID 398632Notes

Reaction equation

HRID 398632 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 at 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. temperatureat 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-801757549b0647fbbee5a399adc2c614
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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