Methyl 3-iodo-4-methylbenzoate → Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

HRID 1488013Notes

Reaction equation

HRID 1488013 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[B:12]1[O:16][C:15]([CH3:18])([CH3:17])[C:14]([CH3:20])([CH3:19])[O:13]1.I[C:22]1C(C)=CC(C)=C(C=1)C(OC)=O.IC1C=C(C=CC=1C)C(OC)=O>>[CH3:22][C:10]1[CH:11]=[C:2]([CH3:1])[C:3]([B:12]2[O:13][C:14]([CH3:20])([CH3:19])[C:15]([CH3:18])([CH3:17])[O:16]2)=[CH:4][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 3

HCID 13614033Methyl 3-iodo-4-methylbenzoateHCID 44828936Methyl 5-iodo-2,4-dimethylbenzoate2×HCID 532171365-Methoxycarbonyl-2-methylphenylboronic acid pinacol ester

Product 1

HCID 59224686Methyl 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Procedure

The title compound was prepared using standard chemical manipulations and procedures similar to those used for the preparation of compound 5.4, except methyl 5-iodo-2,4-dimethylbenzoate (compound 31.1) was used in place of methyl 3-iodo-4-methylbenzoate (compound 5.3). m/z (ES+) 291(M+H)+.

Sources & evidence

ORD record
ord-154dfedacaa44dabbd498aae92a58b44
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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