Triethylamine → 1-Bromo-4-isocyanato-2-(pentafluoro-lambda6-sulfanyl)benzene
Reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[S:9]([F:14])([F:13])([F:12])([F:11])[F:10].Cl[C:16](Cl)([O:18]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.CCCCCC.CCOC(C)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]=[C:16]=[O:18])=[CH:4][C:3]=1[S:9]([F:14])([F:10])([F:11])([F:12])[F:13]Participants
Conditions
- Temperature
- 72 °C
Procedure
To a solution of 4-bromo-3-(pentafluoro-λ6-sulfanyl)aniline (2.36 g, 7.92 mmol, 1.0 eq) in toluene (70 mL) was added triphosgene (1.57 g, 5.3 mmol, 0.67 eq) under N2 at room temperature. Triethylamine (1.31 mL, 9.37 mmol, 1.2 eq) was added dropwise by syringe. The mixture was stirred at 72° C. (oil bath) for 2 hrs. TLC (hexane/EtOAc=2/1, UV) indicated that starting material was consumed. The mixture was allowed to cool to room temperature. Hexane (100 mL) was added. The precipitate was removed by filtration, washed with hexane (30 mL). The combined filtrate was concentrated by evaporator in vacuo at 70° C. for 40 min to afford crude 1-bromo-4-isocyanato-2-(pentafluoro-λ6-sulfanyl)benzene as a brown liquid which was used immediately for the next reaction without further purification.
Workup
- customwas consumed
- temperatureto cool to room temperature
- additionHexane (100 mL) was added
- customThe precipitate was removed by filtration
- washwashed with hexane (30 mL)
- concentrationThe combined filtrate was concentrated by evaporator in vacuo at 70° C. for 40 min
Sources & evidence
- ORD record
- ord-c57fb84d6d704e52b86bdd7fa8727068
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08937088B2
Reaction notes
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