Hydrochloric Acid → HCID 23577141, compound

HRID 908053Notes

Reaction equation

HRID 908053 reaction equation
O[C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C=CC=CC=1.[F:21][C:22]([F:35])([F:34])[S:23]([O:26]S(C(F)(F)F)(=O)=O)(=[O:25])=[O:24].[ClH:36].C([O-])(O)=O.[Na+]>ClCCl>[Cl:36][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:26][S:23]([C:22]([F:35])([F:34])[F:21])(=[O:24])=[O:25])/[CH:8]=[CH:2]/[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 67389927HCID 67389927, compound

Product 1

HCID 23577141HCID 23577141, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To the ethyl hydroxycinnamate (5.02 g, 22.1 mmol), prepared in Step 3, and pyridine (4.0 mL, 50.0 mmol) in dichloromethane (50 mL) at 0° C. under argon was added trifluoromethanesulfonic anhydride (4.0 mL, 23.7 mmol) over a 30-minute period. The mixture was stirred for 4 hours, warmed to 20° C., then worked-up (10% hydrochloric acid and 5% NaHCO3 washes) to afford ethyl (E)-3-chloro-4-(trifluoromethanesulfonyloxy)cinnamate as a white solid (7.90 g, 98% yield): m.p. 59-61° C.; Rf0.49 (20% ethyl acetate/hexane); 1H NMR spectrum (300 MHz, CDCl3) δ 1.35 (t, J=7.1 Hz, 3, CH3), 4.28 (q, J=7.1 Hz, 2, CH2), 6.45 (d, J=16.0 Hz, 1, HC═CCO), 7.38 (d, J=8.5 Hz, 1, ArH), 7.48 (dd, J=8.5, 1.8 Hz, 1, ArH), 7.59 (d, J=16.0 Hz, 1, C═CHCO), 7.67 ppm (d, J=1.9 Hz, 1, ArH).

Sources & evidence

ORD record
ord-38119df0d9524a7b8180be6a9ebd1dc2
Source dataset
uspto-grants-2011_09
Patent number
USRE042700E1

Reaction notes

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