Methanol → Methyl 2-fluoro-3-nitrobenzoate

HRID 239252Notes

Reaction equation

HRID 239252 reaction equation
[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[CH3:19]O>>[F:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:19])=[O:5]

Participants

4

Conditions

Temperature
70 °C

Procedure

2-Fluoro-3-nitrobenzoic acid (75 g) was dissolved in 300 ml of methanol, and then 20 ml of concentrated H2SO4 was added. The mixture was stirred at 70° C. overnight and cooled to rt, the resulting solid was filtered and washed with water (3×200 ml), to the filtered was added water (400 ml), the resulting precipitate was filtered and washed with water (2×100 ml) to afford another batch of product. The solid were combined and dried under vacuum to afford the title compound was obtained as a light yellow solid (78 g, 96%).

Workup

  1. temperaturecooled to rt
  2. filtrationthe resulting solid was filtered
  3. washwashed with water (3×200 ml), to the filtered
  4. additionwas added water (400 ml)
  5. filtrationthe resulting precipitate was filtered
  6. washwashed with water (2×100 ml)
  7. customto afford another batch of product
  8. customdried under vacuum

Sources & evidence

ORD record
ord-e37aa0f5049040618f2d04b983fcc7c7
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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