Triethylamine → Methyl 3-Cyano-4-(trifluoromethylsulfonyloxy)benzoate

HRID 1771471Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].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(Cl)Cl.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][S:22]([C:25]([F:28])([F:27])[F:26])(=[O:23])=[O:21])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

Conditions

Temperature: 30 °C

Procedure

To a mixture of crude methyl 3-cyano-4-hydroxybenzoate (2.50 g) from above and Et3N (1.31 g, 13.0 mmol) in anhydrous DCM (20 mL) was added Tf2O (1.82 g, 6.50 mmol) dropwise and then the reaction mixture was stirred at 30° C. for 2 hours. The resulting mixture was suspended in water (50 mL) and extracted with DCM (50 mL×3), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (PE/EtOAc=10/1) to give Intermediate 1 (550 mg, 2-step yield: 28%) as a colorless oil. 1H NMR (CDCl3 300 MHz): δ 8.43 (d, J=2.1 Hz, 1H), 8.37 (dd, J=8.7, 2.1 Hz, 1H), 7.59 (d, J=8.7 Hz, 1H), 3.98 (s, 3H).

Workup

extractionextracted with DCM (50 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified by column chromatography on silica gel (PE/EtOAc=10/1)

Sources & evidence

ORD record: ord-5b88eb5f925d44129e0fe6d39e7a0473
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249132B2

Reaction notes

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