Pyridine → 2,2-Dimethylpropyl 2-methyl-4-bromobenzoate

HRID 24169

Reaction equation

HRID 24169 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][C:13]([CH3:17])([CH3:16])[CH2:14]O.N1C=CC=CC=1>O=S(Cl)Cl>[CH3:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][C:13]([CH3:17])([CH3:16])[CH3:14])=[O:5]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6404Neopentyl alcoholHCID 995704-Bromo-2-methylbenzoic acid

Product 1

HCID 225689392,2-Dimethylpropyl 2-methyl-4-bromobenzoateYield 68%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

Using General Esterification Method C; 2-methyl-4-bromo-benzoic acid (1.82 g, 8.47 mmols) was refluxed for 3 h with 10 mL SOCl2. The resulting solution was concentrated under reduced pressure and the crude acyl chloride combined with 2,2-dimethylpropanol (0.75 g, 8.47 mmols) and pyridine (1.4 mL, 16.9 mmols) to give the title compound (1.64 g, 68%) after work-up and column chromatography (2-5% EtOAc—hexanes) as a colorless oil.

Workup

  1. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-63449081144e47959fac4c07d18503df
Source dataset
uspto-grants-2005_02
Patent number
US06855512B2

Linked notes

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