3-Fluoro-4-hydroxybenzeneacetic acid → Methyl 2-(3-fluoro-4-hydroxyphenyl)acetate

HRID 453508

Reaction equation

HRID 453508 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].[Si](C=[N+]=[N-])(C)(C)[CH3:14]>C1COCC1.CO>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([O:12][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 680143-Fluoro-4-hydroxybenzeneacetic acidHCID 167693Trimethylsilyldiazomethane

Product 1

HCID 10797559Methyl 2-(3-fluoro-4-hydroxyphenyl)acetateYield 64.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-(3-Fluoro-4-hydroxyphenyl)acetic acid (1.0 g, 5.88 mmol) was diluted with THF:MeOH (3:1) (10 mL) followed by the addition of TMSCHN2 (5.88 ml, 11.8 mmol). After stirring for 1 hour, the reaction was quenched with 2N HCl and diluted with DCM. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (2:1) to yield methyl 2-(3-fluoro-4-hydroxyphenyl)acetate (700 mg, 64.7% yield) as a clear oil.

Workup

  1. customthe reaction was quenched with 2N HCl
  2. additiondiluted with DCM
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material was purified by silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-7e60a6359e424f16becd7cc037e0ee9c
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Linked notes

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