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

HRID 2380209Notes

Reaction equation

HRID 2380209 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-46e94d81598c47a7b9872e9ce6703792
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Reaction notes

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