3-tert-Butyl-6-methylsalicylic acid → 3-Bromo-5-tert-butyl-6-hydroxy-2-methylbenzoic acid

HRID 2398820Notes

Reaction equation

HRID 2398820 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])=[C:8]([OH:13])[C:9]=1[C:10]([OH:12])=[O:11]>C(O)(=O)C>[Br:1][C:5]1[C:4]([CH3:3])=[C:9]([C:10]([OH:12])=[O:11])[C:8]([OH:13])=[C:7]([C:14]([CH3:17])([CH3:16])[CH3:15])[CH:6]=1

Participants

4

Reactant 2

HCID 233613-tert-Butyl-6-methylsalicylic acidHCID 24408Bromine

Product 1

HCID 214341203-Bromo-5-tert-butyl-6-hydroxy-2-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 16.8 g. of bromine in 105 g. of glacial acetic acid is added during 80 minutes to a stirred solution of 20.8 g. of 6-methyl-3-t-butylsalicylic acid in 190 g. of glacial acetic acid, and the mixture is stirred at laboratory temperature for a further 1 hour and then poured into 500 ml. of an ice-water mixture. The mixture is filtered and there is thus obtained as solid residue 5-bromo-6-methyl-3-t-butylsalicylic acid, m.p. 212°-214° C.

Workup

  1. additionpoured into 500 ml
  2. filtrationThe mixture is filtered

Sources & evidence

ORD record
ord-8aa2083bd70347afb1e5045a519f8600
Source dataset
uspto-grants-1977_05
Patent number
US04025647

Reaction notes

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