Tert-Butyl nitrite → Benzene, 1-bromo-2-(methylthio)-4-(trifluoromethyl)-

HRID 21462

Reaction equation

HRID 21462 reaction equation
N(OC(C)(C)C)=O.N[C:9]1[CH:10]=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:12]=[CH:13][C:14]=1[Br:15].[CH3:20][S:21]SC>C(Cl)(Cl)Cl>[Br:15][C:14]1[CH:13]=[CH:12][C:11]([C:16]([F:19])([F:18])[F:17])=[CH:10][C:9]=1[S:21][CH3:20]

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitrite2×HCID 12232Dimethyl DisulfideHCID 679892-Bromo-5-(trifluoromethyl)benzenamine2×

Product 1

HCID 11000144Benzene, 1-bromo-2-(methylthio)-4-(trifluoromethyl)-

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

t-Butyl nitrite (3 ml) was added to a mixture of 3-amino-4-bromobenzotrifluoride (4 g) and dimethyl disulphide (15 ml) in chloroform. The mixture was warmed until reaction started when t-butyl nitrite (11 ml) and a solution of 3-amino-4-bromobenzotrifluoride (16 g) in chloroform were added simultaneously. The resultant mixture was stirred for 24 hours, washed with water, hydrochloric acid (2M), water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give 4-bromo-3-(methylsulphenyl)benzotrifluoride (16.4 g) as a yellow oil, b.p. 84°-88° C. at 2 mm Hg.

Workup

  1. temperatureThe mixture was warmed until reaction
  2. washwashed with water, hydrochloric acid (2M), water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. distillationthe residue was distilled

Sources & evidence

ORD record
ord-743f0184faad46bdaf8b57fb69cedb4f
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Linked notes

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