Thiophene, 2,3-bis(4-fluorophenyl)- → HCID 20473437, compound

HRID 2296055Notes

Reaction equation

HRID 2296055 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.C([Li])CCC.[CH3:25][N:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([F:31])([F:30])[F:29]>C(OCC)C>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[CH:11]=[C:10]([C:27]([C:28]([F:29])([F:31])[F:30])([NH:26][CH3:25])[C:32]([F:35])([F:34])[F:33])[S:9][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 11975814Thiophene, 2,3-bis(4-fluorophenyl)-HCID 125081091,1,1,3,3,3-Hexafluoro-N-methylpropan-2-imineHCID 178418339Butyllithium

Product 1

HCID 20473437HCID 20473437, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2,3-bis(4-fluorophenyl)thiophene (5.4 g, 20 mmole) in 150 ml diethyl ether/30 ml toluene was cooled to 10° and treated with 1.6M n-butyl lithium (15 ml, 1.2 equiv.). The reaction mixture was heated at reflux for 1.5 hours, cooled to 0° and treated dropwise with a solution of N-methyl hexafluoroacetone imine (4.3 g, 1.2 equiv.) in 10 ml diethyl ether. The reaction mixture was stirred for 3 hours at 0° and then quenched with water.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled to 0°
  4. customquenched with water

Sources & evidence

ORD record
ord-e23d418588884288b34293840b674aac
Source dataset
uspto-grants-1984_01
Patent number
US04427693

Reaction notes

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