Water → 2'-Fluoro-5'-nitro[1,1'-biphenyl]-3-carboxylic acid

HRID 1731804Notes

Reaction equation

HRID 1731804 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[F:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17].O>S(=O)(=O)(O)O>[F:6][C:7]1[CH:12]=[CH:11][C:10]([N+:1]([O-:4])=[O:2])=[CH:9][C:8]=1[C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 24434Potassium NitrateHCID 27826832'-Fluorobiphenyl-3-carboxylic acid

Product 1

HCID 137328522'-Fluoro-5'-nitro[1,1'-biphenyl]-3-carboxylic acidYield 110.6%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 420 mg potassium nitrate in 5 ml concentrated sulfuric acid was added dropwise to a stirred solution of 1 g 3-(2-fluorophenyl)-benzoic acid in 25 ml concentrated sulfuric acid at 0° C. The mixture was stirred at 0° C. for 20 minutes and then poured into iced water. The resulting precipitate was extracted into ethyl acetate and the extracts were combined, dried and evaporated, yielding the product as a white solid (1.2 g, 100% yield), m.p. 272°-274° C. after recrystallization from ethyl acetate. NMR (DMSO-d6, 250 MHz): 8.4 (m, 2H), 8.16 (d, 1H, J=2 Hz), 8.05 (multiplets, 1H), 7.9 (multiplets, 1H), 7.66 (m, 2H), 3.4 (br s, 1H).

Workup

  1. extractionThe resulting precipitate was extracted into ethyl acetate
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-bc4de5f5d2dc4244bf9ff779f9a40933
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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