Trimethylsilyldiazomethane → Methyl 2-iodo-3-methylbenzoate

HRID 2105043Notes

Reaction equation

HRID 2105043 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].[Si](C=[N+]=[N-])(C)(C)[CH3:13]>C1C=CC=CC=1.CO>[I:1][C:2]1[C:10]([CH3:11])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:13])=[O:5]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 27593652-Iodo-3-methylbenzoic acid

Product 1

HCID 13924925Methyl 2-iodo-3-methylbenzoateYield 91%

Reagents, catalysts & solvents 1

HCID 21927730Benzene methanolSolvent

Procedure

To a solution of 2-iodo-3-methylbenzoic acid (500 mg, 0.48 mmol) in benzene/MeOH (2 mL, 10:1) was added TMSCHN2 (1 mL, 2N), the reaction mixture was stirred at rt for 30 min and then concentrated. The crude product was purified by flash chromatography (0 to 10% EtOAc/Hexanes, gradient) to afford 500 mg (91%) of Intermediate 299.1.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by flash chromatography (0 to 10% EtOAc/Hexanes, gradient)

Sources & evidence

ORD record
ord-ed76db1626e641ac83545614210694c2
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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