Water → HCID 86687949, compound

HRID 2406314Notes

Reaction equation

HRID 2406314 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:14][CH3:15])[CH:3]=1.[B-](F)(F)(F)[F:17].[B-](F)(F)(F)F.C1[N+]2(CCl)CC[N+](F)(CC2)C1.O>C(#N)C>[NH2:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]([O:12][CH3:13])[C:11]=1[F:17]

Participants

5

Reactant 3

HCID 962WaterHCID 2724933SelectfluorHCID 58907369HCID 58907369, compound

Product 1

HCID 86687949HCID 86687949, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 4-amino-2,6-dimethoxybenzoate (510 mg, 2.42 mmol) in acetonitrile (10 mL) at 0° C. was added Selectfluor® (940 mg, 2.66 mmol). The mixture was stirred 30 minutes at 0° C. then water (10 mL) was added. The reaction was extracted twice with ethyl acetate (30 mL). The organic phases were combined, passed through a hydrophobic frit and the solvent was removed in vacuo. Purification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane) gave methyl 4-amino-3-fluoro-2,6-dimethoxybenzoate (114 mg, 20%) as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 6.05 (d, J=6.4 Hz, 1H), 3.93 (s, 3H), 3.88 (s, 3H), 3.75 (s, 3H).

Workup

  1. extractionThe reaction was extracted twice with ethyl acetate (30 mL)
  2. customthe solvent was removed in vacuo
  3. customPurification of the residue via silica gel column chromatography (0-100% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-9ae848a12a6d44d99baba3381052eaf1
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

Loading…