Trifluoroacetic acid → (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetic acid

HRID 726149Notes

Reaction equation

HRID 726149 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12][C:13]2([CH2:20][C:21]([OH:23])=[O:22])O>ClCCl>[Cl:8][C:9]1[CH:17]=[C:16]([F:18])[CH:15]=[C:14]2[C:10]=1[CH2:11][CH2:12]/[C:13]/2=[CH:20]\[C:21]([OH:23])=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 110860282-(4-Chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid

Product 1

HCID 11031575(E)-2-(4-chloro-6-fluoro-1-indanylidene)acetic acidYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (27.4 ml) was added to a stirred, chilled (ice-methanol bath) solution of 2-(4-chloro-6-fluoro-1-hydroxy-1-indanyl)acetic acid (12.5 g, 0.05 mol) in dichloromethane (200 ml). After 1.5 h, the mixture was concentrated in vacuo. Dichloromethane was added to the residue and the mixture was concentrated in vacuo to give 10.6 g of crude (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetic acid. Chromatography of a 1.0 g sample on silica gel with ethyl acetate:hexanes (1:1) as eluent gave 0.32 g of (E)-2-(4-chloro-6-fluoro-1-indanylidene)acetic acid as a white solid: mp 229°-230° C.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionDichloromethane was added to the residue
  3. concentrationthe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-db283d9ef86f4447b37f32f7eedb41f3
Source dataset
uspto-grants-1998_01
Patent number
US05708033

Reaction notes

Loading…