Trimethylsilyldiazomethane → 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].[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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated
- 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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