Sodium Hydroxide → 3′,4′,5′-Trifluoro-2-nitro-1,1′-biphenyl

HRID 534709Notes

Reaction equation

HRID 534709 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]2[C:15](Br)([N+:16]([O-:18])=[O:17])[CH2:14][CH:13]=[CH:12][CH2:11]2)[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[OH-].[Na+]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:5]=[C:6]([F:9])[C:7]=1[F:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 50992665HCID 50992665, compound

Product 1

HCID 509926663′,4′,5′-Trifluoro-2-nitro-1,1′-biphenyl

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 500 mg (1.49 mmol) of 3,4,5-trifluoro-1-(6-bromo-6-nitrocyclohex-3-en-1-yl)-benzene from example 2.4 in 10 ml of toluene were added 200 mg (0.6 mmol) of tetrabutylammonium bromide and 15 ml of aqueous NaOH (4M) and the mixture was stirred for 24 h at room temperature. During the reaction, air was sparged through the mixture. Then the reaction mixture was stirred for another 12 h at 50° C. After cooling to room temperature, the phases were separated, the aqueous phase was extracted with ethylacetate (3×10 ml) and the organic phases were dried over Na2SO4. Column chromatography (SiO2, cyclohexane/ethylacetate 8:1) yielded 218 mg (0.86 mmol, 58% of theory) of the title compound as a reddish solid.

Workup

  1. customDuring the reaction, air
  2. customwas sparged through the mixture
  3. stirringThen the reaction mixture was stirred for another 12 h at 50° C
  4. temperatureAfter cooling to room temperature
  5. customthe phases were separated
  6. extractionthe aqueous phase was extracted with ethylacetate (3×10 ml)
  7. dry with materialthe organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-82f2b567b02943f9aa7010ca2e732a64
Source dataset
uspto-grants-2014_10
Patent number
US08853455B2

Reaction notes

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