Hydrochloric Acid → 3-amino-6-fluorobiphenyl

HRID 1731799Notes

Reaction equation

HRID 1731799 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 18371303HCID 18371303, compound

Product 1

HCID 116655293-amino-6-fluorobiphenylYield 68.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 18.5 g of 4-fluoro-3-phenylnitrobenzene, 76.7 g of stannous chloride dihydrate and 150 ml concentrated hydrochloric acid was heated at 60° C. for 2 hours with stirring. After cooling, the resulting precipitate was dissolved in water and the mixture was basified with sodium carbonate. The mixture was extracted five times with chloroform and the combined organic extracts were dried and evaporated to yield the product as a pale brown oil (10.9 g, yield 68%) which was used without further purification. NMR (CDCl3, 60 MHz): 7.15 (m, 5H), 7.1-6.1 (m, 3H), 3.3 (br,s, 2H).

Workup

  1. temperatureAfter cooling
  2. extractionThe mixture was extracted five times with chloroform
  3. customthe combined organic extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-01343ca0fdb3425490657f5020df19e0
Source dataset
uspto-grants-1986_11
Patent number
US04623650

Reaction notes

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