Nitrous Acid → Methyl 4-fluoro-2-phenylbenzoate

HRID 325210Notes

Reaction equation

HRID 325210 reaction equation
N[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:3]=1.N([O-])=O.[Na+].N(O)=O.[H+].[B-](F)(F)(F)[F:27]>>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([F:27])=[CH:3][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 4

HCID 24529Nitrous AcidHCID 28118Tetrafluoroboric acidHCID 154069885-Amino-biphenyl-2-carboxylic acid methyl esterHCID 23668193Sodium Nitrite

Product 1

HCID 54170746Methyl 4-fluoro-2-phenylbenzoate

Procedure

A solution of methyl 4-amino-2-phenylbenzoate (1.0 equivalent) in dilute aqueous HBF4 is treated with NaNO2 (1.1 equivalents) until an excess of nitrous acid persists. The mixture is extracted into ethyl acetate which is dried and evaporated. The title ester is purified by chromatography on silica gel.

Workup

  1. extractionThe mixture is extracted into ethyl acetate which
  2. customis dried
  3. customevaporated
  4. customThe title ester is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-a59aa93faa34482abdedab2de5b795a3
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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