Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14])[C:7]([OH:9])=O)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:21][Si](C=[N+]=[N-])(C)C.[BrH:28].CC(O)=O.N#N>C(Cl)Cl>[Br:28][CH2:21][C:7]([C:6]1[CH:10]=[CH:11][C:12]([C:13]([F:16])([F:15])[F:14])=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:9]Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
3-Nitro-4-(trifluoromethyl)benzoic acid (Matrix Scientific, 2.35 g, 10 mmol) is dissolved in thionyl chloride (22 mL, 300 mmol). The stirred solution is heated at 95° C. for 16 hr, then cooled, concentrated and CH2Cl2 (51 mL) and trimethylsilyldiazomethane (20 mL, 2 M in Hexanes, 40 mmol) are added and the reaction is stirred for 2 hr at room temp. The mixture is cooled to 0° C. and HBr/HOAc (6.33 mL, 33% of HBr in HOAc) is added dropwise (N2 evolution). After addition the mixture is stirred at 0° C. for 5 min, then concentrated and purified by silica gel chromatography (CH2Cl2) to give the title compound (2.59 g, 83% yield). LCMS m/z=313.5 [M+H]+, tR=2.65 min.
Workup
- temperaturecooled
- concentrationconcentrated
- temperatureThe mixture is cooled to 0° C.
- additionAfter addition the mixture
- stirringis stirred at 0° C. for 5 min
- concentrationconcentrated
- custompurified by silica gel chromatography (CH2Cl2)
Sources & evidence
- ORD record
- ord-e5755538df574e1e83fd0aea75d7ee18
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871767B2
Linked notes
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