Methanol → Methyl 3-amino-5-fluorobenzoate

HRID 521412Notes

Reaction equation

HRID 521412 reaction equation
[NH2:1][C:2]1[C:3](Br)=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([O-:7])=[O:6].[H][H].[CH3:15]O>[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([O:7][CH3:15])=[O:6]

Participants

5

Reactant 3

HCID 887MethanolHCID 863266553-Amino-2-bromo-5-fluorobenzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 3807862Methyl 3-amino-5-fluorobenzoateYield 88%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-amino-2-bromo-5-fluorobenzoate (2.48 g, 10 mmol) in MeOH (80 mL) was added Pd/C (0.5 g, 5%, 50% water), the mixture was stirred at atmosphere of hydrogen for about 6.0 h. Then the mixture was filtered, washed with MeOH (10 mL). The filtrate was concentrated and recrystallized with MeOH (2.5 mL) to afford methyl 3-amino-5-fluorobenzoate (1.48 g, 88%) as a brown solid. 1H NMR (DMSO-d6) δ 7.04 (t, 1H, J=1.8 Hz), 6.74-6.76 (m, 1H), 6.55-6.80 (m, 1H), 6.58 (m, 1H), 3.82 (s, 3H).

Workup

  1. filtrationThen the mixture was filtered
  2. washwashed with MeOH (10 mL)
  3. concentrationThe filtrate was concentrated
  4. customrecrystallized with MeOH (2.5 mL)

Sources & evidence

ORD record
ord-b2c47cdd2fd2434da24bd6b551f58265
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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