Trifluoroacetic acid → HCID 86711195, compound

HRID 1850756Notes

Reaction equation

HRID 1850756 reaction equation
[CH:1]1([C:4]([C:6]2[C:11]([F:12])=[CH:10][C:9]([O:13]CC3C=CC(OC)=CC=3)=[CH:8][C:7]=2[F:23])=[O:5])[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:1]1([C:4]([C:6]2[C:7]([F:23])=[CH:8][C:9]([OH:13])=[CH:10][C:11]=2[F:12])=[O:5])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70818711HCID 70818711, compound

Product 1

HCID 86711195HCID 86711195, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of cyclopropyl {2,6-difluoro-4-[(4-methoxybenzyl)oxy]phenyl}methanone (700 mg, 2.20 mmol) in DCM (10 ml) was added to TFA (3.0 mL) and the resulting solution stirred for 2 hour at RT. The material was concentrated under reduced pressure and the residue purified via flash column chromatography (80 g silica gel, ISCO, eluting with 30-100% ethyl acetate in hexane) to afford the title compound as an oil. 1H NMR (CDCl3): δ 8.20 (s, 2H), δ 2.43-2.38 (m, 1H), δ 1.35-1.28 (m, 2H), δ 1.10-1.03 (m, 2H). LC/MS 221 (M+Na)+.

Workup

  1. concentrationThe material was concentrated under reduced pressure
  2. customthe residue purified via flash column chromatography (80 g silica gel, ISCO, eluting with 30-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-058ab00537fe478dbb3c9343c9027f45
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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