Methyl iodide → Methyl 4-chloro-2-iodo-6-methylbenzoate

HRID 2427670Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:5]([C:6]([OH:8])=[O:7])=[C:4]([I:12])[CH:3]=1.[C:13]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:13][O:7][C:6](=[O:8])[C:5]1[C:9]([CH3:11])=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[I:12]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 4-chloro-2-iodo-6-methyl-benzoic acid (5.9 g, 20.0 mmol) in acetone (50 mL) was treated with anhydrous K2CO3 (4.14 g, 30 mmol) followed by methyl iodide (1.5 g, 24 mmol). The reaction mixture was stirred at 70° C. for 2 h. GC-MS and TLC indicated that the reaction was completed. The solids were removed by filtration and the filtrate was evaporated under reduced pressure. Silica gel column chromatography of the resulting material using 10% ethyl acetate in hexanes afforded 4-chloro-2-iodo-6-methyl-benzoic acid methyl ester (2.91 g, 47%). GC-MS: m/z 310 (M)+, 279 (M−31)+.

Workup

customThe solids were removed by filtration
customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-12d80c6ef3a54286a0429c15062c9037
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968570B2

Reaction notes

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