Phenol → 3-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzoic acid phenyl ester

HRID 910007Notes

Reaction equation

HRID 910007 reaction equation
[Br:1][C:2]1[C:3]([CH3:16])=[C:4]([C:8]([OH:15])=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6].[C:17]1(O)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[C:17]1([O:6][C:5](=[O:7])[C:4]2[C:8]([OH:15])=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[CH:10]=[C:2]([Br:1])[C:3]=2[CH3:16])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 24813Phosphorus oxychlorideHCID 214341203-Bromo-5-tert-butyl-6-hydroxy-2-methylbenzoic acid

Product 1

HCID 574214533-Bromo-5-tert-butyl-6-hydroxy-2-methyl-benzoic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

From 3-bromo-5-tert-butyl-6-hydroxy-2-methyl-benzoic acid, phenol and phosphorus oxychloride in toluene; amber oil; 1H NMR (CDCl3): δ 11.10 (s, 1H), 7.64 (s, 1H), 7.50-7.42 (m, 2H), 7.36-7.28 (m, 1H), 7.22-7.17 (m, 2H), 2.74 (s, 3H), 1.40 (s, 9H); LC-MS: Major component: m/z 269/270 (acylium ion), 363/365 (M+H), 385/387 (M+Na); Rt=2.95 min. The crude product was used without purification.

Workup

  1. customThe crude product was used without purification

Sources & evidence

ORD record
ord-1b2d6316dd994394b75364ba78bb3dbe
Source dataset
uspto-grants-2011_09
Patent number
US08022066B2

Reaction notes

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