Water → 4'-(Trifluoromethyl)-4-biphenylcarbaldehyde

HRID 463514

Reaction equation

HRID 463514 reaction equation
[Li+].CCC[CH2-].Br[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.CN(C)[CH:25]=[O:26].O>CCCCCC.C1COCC1>[F:20][C:19]([F:22])([F:21])[C:16]1[CH:17]=[CH:18][C:13]([C:10]2[CH:11]=[CH:12][C:7]([CH:25]=[O:26])=[CH:8][CH:9]=2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 61028n-Butyl lithiumHCID 127123494-Bromo-4'-(trifluoromethyl)biphenyl

Product 1

HCID 27827124'-(Trifluoromethyl)-4-biphenylcarbaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

N-Butyllitium in hexane (95 ml, 1.55M) was added dropwise to 4-Bromo-4'-trifluoromethylbiphenyl (40 g) in 250 ml of THF under N2 at -70° C. After addition the mixture was stirred for a further 10 mins and then dry dimethylformamide (19.49) in a solution of dry tetrahydrofuran (100 ml) was added dropwise. The mixture was then allowed to warm to room temperature in the absence of coolant. After stirring for 1.5 hours water was added and the mixture extracted with ether. The water washed and dried extracts were evaporated to give p-(4-trifluoromethylphenyl)benzaldehyde (34.5 g) m.p. 70°.

Workup

  1. additionAfter addition the mixture
  2. additionwas added
  3. extractionthe mixture extracted with ether
  4. washThe water washed
  5. customdried extracts
  6. customwere evaporated

Sources & evidence

ORD record
ord-9d36cafe6e454d688a6364df5c155b1a
Source dataset
uspto-grants-1985_05
Patent number
US04520007

Linked notes

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