2-Iodo-3-methylbenzoic acid → Methyl 2-iodo-3-methylbenzoate

Reaction equation

[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](Cl)Cl.CO>>[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:12])=[O:5]

Participants

Reactant 2

HCID 27593652-Iodo-3-methylbenzoic acid

HCID 21226129Dichloromethane methanol

Product 1

HCID 13924925Methyl 2-iodo-3-methylbenzoate

Procedure

2-iodo-3-methylbenzoic acid (595 mg, 2.27 mmol) was dissolved in DCM/MeOH=1/1 (5 ml) at 0° C., then TMS-CH2N2 (2M in Et2O, 1.4 ml, 2.8 mmol) was added. After 1.5 hours at RT solvents were evaporated. Yield 630 mg yellow oil.

Workup

customAfter 1.5 hours at RT solvents were evaporated

Sources & evidence

ORD record: ord-8262197c8ae54385a67703552e0e64e3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062033B2

Reaction notes

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