Methanol → Methyl 2-(2-iodophenyl)acetate

HRID 1642784Notes

Reaction equation

HRID 1642784 reaction equation
C[Si](C=[N+]=[N-])(C)C.[I:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([OH:18])=[O:17].[CH3:19]O>C(Cl)Cl>[CH3:19][O:17][C:16](=[O:18])[CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[I:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 27800902-Iodophenylacetic acid

Product 1

HCID 640185Methyl 2-(2-iodophenyl)acetateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trimethylsilyl diazomethane (15.3 ml, 30.6 mmol, 2.0 M in diethyl ether) was added dropwise to a stirred, cooled 0° C. solution of (2-iodophenyl)acetic acid (4.0 g, 15.3 mmol) and MeOH (10 ml) in CH2Cl2 (50 ml) and the solution was stirred at 0° C. for 1 hour. The yellow solution was purged with nitrogen for 10 minutes. The solvent removed in vacuo and the residue was azeotroped with THF (3×25 ml) to afford 4.2 g, 100% of 23-1 as a yellow oil.

Workup

  1. customThe yellow solution was purged with nitrogen for 10 minutes
  2. customThe solvent removed in vacuo
  3. customthe residue was azeotroped with THF (3×25 ml)

Sources & evidence

ORD record
ord-d860ee30052a4724a85288e43eea1749
Source dataset
uspto-grants-2012_02
Patent number
US08119681B2

Reaction notes

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