1,1-Dichloroethane → HCID 11231977, compound

HRID 1867228Notes

Reaction equation

HRID 1867228 reaction equation
FC(F)(F)S(O)(=O)=O.ClC(Cl)C.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[C:21]([CH3:23])[CH3:22].[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]([C:34]#[N:35])[CH:25]=1>O>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:15]=1[CH2:20][C:21]([CH3:23])([CH3:22])[N:35]=[C:34]2[C:26]1[CH:25]=[N:24][C:33]2[C:28]([CH:27]=1)=[CH:29][CH:30]=[CH:31][CH:32]=2

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 62406Trifluoromethanesulfonic acidHCID 931773-QuinolinecarbonitrileHCID 23193754HCID 23193754, compound

Product 1

HCID 11231977HCID 11231977, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoromethane sulfonic acid (0.52 mL) were added while cooling with ice to a dichloroethane (0.58 mL) solution of an about 4:7 mixture of 1-fluoro-(2-methylpropen-1-yl)benzene and 1-fluoro-(2-methylpropen-2-yl)benzene (87.3 mg, 0.58 mmol) and quinoline-3-carbonitrile (89.6 mg, 0.58 mmol), and after stirring for 18 hours at room temperature, the solution was poured into water followed by extraction with ethyl acetate and applying the resulting residue to chromatography to obtain 82.2 mg of the target compound (yield: 47%).

Workup

  1. extractionfollowed by extraction with ethyl acetate

Sources & evidence

ORD record
ord-326542b25f4143589828a1ae1892b7bb
Source dataset
uspto-grants-2009_12
Patent number
US07632783B2

Reaction notes

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