Triethylamine → Methyl 3-Cyano-4-(trifluoromethylsulfonyloxy)benzoate
Reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]#[N:12])[CH:5]=1.CCN(CC)CC.[O:21](S(C(F)(F)F)(=O)=O)[S:22]([C:25]([F:28])([F:27])[F:26])(=O)=[O:23].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([O:10][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:23])=[O:21])=[C:6]([C:11]#[N:12])[CH:5]=1Participants
6
Conditions
- Temperature
- 0 °C
Procedure
3-cyano-4-hydroxybenzoic acid methyl ester from example 51, step 1 (2 g, 11.3 mmol) was dissolved in CH2Cl2 (57 ml) and cooled to 0° C. in an ice bath. The mixture was treated with Et3N (3 ml, 22.6 mmol) followed by the addition of Tf2O (1.9 ml, 11.3 mmol). The reaction mixture was warmed to room temp. and stirred for 4 hours. Saturated NaHCO3 (10 mL) was added and the mixture was extracted with EtOAc (2×10 mL). The organic layers were combined and dried (MgSO4), filtered, and concentrated. The residue was then purified by flash chromatography (15% EtOAc/Hexane) to yield the desired product.
Workup
- temperatureThe reaction mixture was warmed to room temp.
- extractionthe mixture was extracted with EtOAc (2×10 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
- customThe residue was then purified by flash chromatography (15% EtOAc/Hexane)
Sources & evidence
- ORD record
- ord-8434b885ff4f43ae9460551a8ed99495
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06077853
Reaction notes
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