Sodium Chloride → Methyl 2-(4-fluoroanilino)-4-hydroxybenzoate

HRID 2191635Notes

Reaction equation

HRID 2191635 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([NH:6][C:7]2[CH:16]=[C:15]([O:17]C)[CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.B(Br)(Br)Br.ClCCl.[Cl-].[Na+]>C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7]2[CH:16]=[C:15]([OH:17])[CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 22277759Boron tribromide dichloromethaneHCID 57667822Methyl 2-(4-fluoroanilino)-4-methoxybenzoate

Product 1

HCID 57667875Methyl 2-(4-fluoroanilino)-4-hydroxybenzoateYield 28.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(4-fluoroanilino)-4-methoxybenzoate 2.2 g was added to 1.0 mol/L boron tribromide/dichloromethane 24 mL, and it was stirred at room temperature for 5 hours. Saturated sodium chloride aqueous solution and ethyl acetate were added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Fuji SILYSIA Chemical Ltd., PSQ100B(spherical type), eluent; hexane:ethyl acetate=5:1] to give methyl 2-(4-fluoroanilino)-4-hydroxybenzoate 0.60 g of purple solid.

Workup

  1. customThe organic layer was separated
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3e1037582da54f39969446b654389020
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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