Methanol → Methyl 6-fluoro-3-iodo-2-methylbenzoate

HRID 1948669Notes

Reaction equation

HRID 1948669 reaction equation
C[Si](C=[N+]=[N-])(C)C.[F:8][C:9]1[C:14]([C:15]([OH:17])=[O:16])=[C:13]([CH3:18])[C:12]([I:19])=[CH:11][CH:10]=1.[CH3:20]O>C1C=CC=CC=1>[F:8][C:9]1[C:14]([C:15]([O:17][CH3:20])=[O:16])=[C:13]([CH3:18])[C:12]([I:19])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 594505486-Fluoro-3-iodo-2-methylbenzoic acid

Product 1

HCID 59450535Methyl 6-fluoro-3-iodo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Trimethylsilyldiazomethane solution (2 M in Hexane) (18 mL, 35 mmol) was added dropwise to a stirred solution of the product of Step A (7.3 g, 33.2 mmol) in benzene containing 20% of methanol (total: 100 mL) at room temperature until solution retained a yellow color. The mixture was concentrated to remove the organic solvent. The remaining oil was poured over a silica gel plug in a 60-mL filter frit funnel and eluting with 200 mL of hexane containing 10% ethyl acetate. The filtrate was then concentrated to dryness to give the title compound as a bright yellow oil.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove the organic solvent
  3. additionThe remaining oil was poured over a silica gel plug in a 60-mL
  4. filtrationfilter frit funnel
  5. washeluting with 200 mL of hexane containing 10% ethyl acetate
  6. concentrationThe filtrate was then concentrated to dryness

Sources & evidence

ORD record
ord-02f00273b72c43bfbe4c0149769ce382
Source dataset
uspto-grants-2013_03
Patent number
US08399507B2

Reaction notes

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