Triethylamine → 4-(6-Bromonaphth-2-ylthio)-2-trifluoromethylbenzonitrile

HRID 346677Notes

Reaction equation

HRID 346677 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([SH:12])[CH:6]=[CH:5]2.F[C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:15]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12][C:14]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([C:22]([F:23])([F:25])[F:24])[CH:15]=1)[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrileHCID 197648176-Bromonaphthalene-2-thiol

Product 1

HCID 179157914-(6-Bromonaphth-2-ylthio)-2-trifluoromethylbenzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-bromonaphthalene-2-thiol (956 mg) and 4-fluoro-2-trifluoromethyl benzonitrile (756 mg) in dimethylformamide (15 ml), at ambient temperature, was treated dropwise with triethylamine (504 mg). After stirring at ambient temperature for 3 hours the reaction mixture was diluted with ethyl acetate (100 ml), washed with water (3×25 ml) and brine (25 ml), dried (MgSO4) and evaporated to give a yellow oil. Crystallisation from methanol (20 ml) gave 4-(6-bromonaphth-2-ylthio)-2-trifluoromethylbenzonitrile (1.176 g, mp 114-116° C.;

Workup

  1. washwashed with water (3×25 ml) and brine (25 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customto give a yellow oil
  5. customCrystallisation from methanol (20 ml)

Sources & evidence

ORD record
ord-b672429898944e23b01a2d853ad34746
Source dataset
uspto-grants-2007_02
Patent number
US07173025B1

Reaction notes

Loading…