Trifluoroacetic anhydride → HCID 11817048, compound

HRID 2083904Notes

Reaction equation

HRID 2083904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[C:4]([O:14][CH3:15])[CH:3]=1.[B-](F)(F)(F)[O+](C)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[C:4]([O:14][CH3:15])[CH:3]=1)[S:8][CH2:9][CH2:10][C:11]2=[O:13]

Participants

5

Reactant 3

HCID 9845Trifluoroacetic anhydrideHCID 22731982HCID 22731982, compoundHCID 178494437HCID 178494437, compound

Product 1

HCID 11817048HCID 11817048, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution/suspension of 3-(4-chloro-2-methoxyphenylthio)propanoic acid (1.46 g, 5.92 mmol; see step (ii) above) in dichloromethane (50 mL) under N2(g) was added boron trifluoride dimethyl etherate (1.4 mL, 15 mmol) and trifluoroacetic anhydride (2.1 mL, 15 mmol). After 2.5 h at rt the reaction was quenched with water (2 mL), then washed with more water. The deep green colour disappeared when it was further washed with sat. aq. sodium hydrogencarbonate. Drying (MgSO4) and removal of the solvent in vacuo afforded the sub-title compound as a yellow solid.

Workup

  1. customAfter 2.5 h at rt the reaction was quenched with water (2 mL)
  2. washwashed with more water
  3. washwas further washed with sat. aq. sodium hydrogencarbonate
  4. customDrying
  5. custom(MgSO4) and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-ec772d34be0044f18172b70733caed02
Source dataset
uspto-grants-2004_04
Patent number
US06716834B2

Reaction notes

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