Methanol → Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

HRID 604663Notes

Reaction equation

HRID 604663 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([OH:13])=[O:12].CO.[Si](C=[N+]=[N-])(C)(C)[CH3:17]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH2:10][C:11]([O:13][CH3:17])=[O:12]

Participants

5

Reactant 3

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 193619782-(2-Fluoro-4-methoxyphenyl)acetic acid

Product 1

HCID 21472203Methyl 2-(2-fluoro-4-methoxyphenyl)acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (2-fluoro-4-methoxyphenyl)acetic acid (500 mg, 2.72 mmol) in toluene (20 mL) was added MeOH (3 mL) and TMS diazomethane (2.04 mL of a 2M solution in hexanes, 4.08 mmol). After 15 min, the reaction was quenched by the addition of HOAc (250 μL). The reaction was diluted with EtOAc (100 mL) and washed with saturated NaHCO3 (2×25 mL) and brine (25 mL). The organic layer was dried (Na2SO4), filtered and concentrated. Purification of the residue by flash chromatography (0 to 25% EtOAc/hexanes) afforded methyl (2-fluoro-4-methoxyphenyl)acetate. 1H NMR (500 MHz, CDCl3): δ 7.15 (t, J=8.6 Hz, 1H), 6.62-6.68 (m, 2H), 3.78 (s, 3H), 3.70 (s, 3H), 3.60 (s, 2H).

Workup

  1. customthe reaction was quenched by the addition of HOAc (250 μL)
  2. additionThe reaction was diluted with EtOAc (100 mL)
  3. washwashed with saturated NaHCO3 (2×25 mL) and brine (25 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography (0 to 25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-6df4557615804591b33a204f8a249f4c
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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