Hydrochloric Acid → Methyl 2-fluoro-3-iodo-4-methylbenzoate

HRID 555172Notes

Reaction equation

HRID 555172 reaction equation
[F:1][C:2]1[C:10]([I:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.[CH3:14]O>>[F:1][C:2]1[C:10]([I:11])=[C:9]([CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:14])=[O:5]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 593839002-Fluoro-3-iodo-4-methylbenzoic acid

Product 1

HCID 67211177Methyl 2-fluoro-3-iodo-4-methylbenzoate

Conditions

Temperature
80 °C

Procedure

To the solution of 2-fluoro-3-iodo-4-methylbenzoic acid (450 mg, 1.6 mmol, 1.0 eq) in methanol (5 ml), catalytic amount of conc.HCl (0.1 ml) was added. The resultant solution was heated to reflux at 80° C. for overnight. Methanol was evaporated. To this residue, water was added and the aqueous layer was extracted thrice with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulphate, filtered and evaporated to afford methyl 2-fluoro-3-iodo-4-methylbenzoate. Yield: 450 mg (95%). 1H NMR (400 MHz, DMSO): δ 2.49 (s, 3H), 3.85 (s, 3H), 7.30-7.32 (d, 1H, J=7.84 Hz), 7.76-7.80 (t, 1H, J=7.82 Hz). LCMS: (ES+) m/z=295 (M+H).

Workup

  1. customMethanol was evaporated
  2. additionTo this residue, water was added
  3. extractionthe aqueous layer was extracted thrice with ethyl acetate
  4. dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-952b63d9280942bab96fac29e82b13e8
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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