P-Toluic Acid → 4-(Bromomethyl)benzoic acid

HRID 355230Notes

Reaction equation

HRID 355230 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=[O:9])=[CH:6][CH:7]=1.[Br:11]N1C(=O)CCC1=O>C1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:11][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7470P-Toluic AcidHCID 67184N-bromobutanimide

Product 1

HCID 225994-(Bromomethyl)benzoic acidYield 71.1%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 241BenzeneSolvent

Procedure

A mixture (suspension) of p-toluic acid (13.6 g, 98 mmol), N-bromosuccinimide (17.8 g, 99 mmol) and benzoylperoxide (0.2 g, 0.826 mmol) in dry benzene (100 ml) was heated at reflux for 21 h. After evaporation of the solvent in vacuo, the white residual solid was suspended in boiling water (100 ml), collected by filtration and washed with boiling water (4×100 ml). The crude dried product was crystallized from hot MeOH, yielding 15.0 g (69.7 mmol, 71.1%) of p-bromomethylbenzoic acid as white crystals mp 223°-225° C.; 1Hmr (DMSO-d6)δ: 4.75 (2H, s, --CH2Br), 7.47-7.62-7.88-8.02 ppm (4H, A2 'B2 ', aromatic Hs); ir (nujol) νmax : 2500-2600 (br.--CO2H), and 1670 cm-1 (C=O--CO2H). Procedure of D. H. Rich and S. K. Gurmura, J. Am. Chem. Soc., 97 1575 (1975).

Workup

  1. temperatureat reflux for 21 h
  2. customAfter evaporation of the solvent in vacuo
  3. filtrationcollected by filtration
  4. washwashed with boiling water (4×100 ml)
  5. customThe crude dried product was crystallized from hot MeOH

Sources & evidence

ORD record
ord-d9ffb1f829af48c38151b636117a5389
Source dataset
uspto-grants-1983_03
Patent number
US04378314

Reaction notes

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