Benzoyl Peroxide → 7-Bromomethylnaphthalene-1-carboxylic acid

HRID 496323Notes

Reaction equation

HRID 496323 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[C:20]([OH:22])=[O:21])=[CH:12][CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:1][CH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[C:20]([OH:22])=[O:21])=[CH:12][CH:11]=1

Participants

4

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 136680487-Methylnaphthalene-1-carboxylic acid

Product 1

HCID 121243507-Bromomethylnaphthalene-1-carboxylic acidYield 96.7%

Procedure

A suspension of N-bromosuccinimide (6.23 g, 0.035 mol) in a solution of 7-methylnaphthalene-1-carboxylic acid (6.2 g, 0.033 mol) in tetrachlomethane (200 mL) was refluxed in the presence trace amounts of benzoyl peroxide for 2 hours. The resulting white suspension was evaporated to dryness under reduced pressure, washed with hot water and dried to give the crude product (8.46 g, 95.8%). An analytical sample was recrystallized from benzene-ethanol mixture. M.p. 209.5-211° C. 1H NMR δ 13.20 (bs, 1H), 8.91 (bs, 1H), 8.30-7.95 (m, 3H), 7.72-7.54 (m, 2H), 4.92 (s, 2H). Anal. Calcd for C12H9BrO2: C, 54.37; H, 3.42. Found: C, 54.45; H, 3.44.

Workup

  1. customThe resulting white suspension was evaporated to dryness under reduced pressure
  2. washwashed with hot water
  3. customdried

Sources & evidence

ORD record
ord-7da35c77379246ea95a81008b76a7ad1
Source dataset
uspto-grants-2005_09
Patent number
US06943267B1

Reaction notes

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