Trifluoroacetic acid → 4-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

HRID 1626488Notes

Reaction equation

HRID 1626488 reaction equation
C([O:5][C:6]([C:8]1[CH:30]=[CH:29][C:11]([O:12][C:13]2[CH:22]=[C:21]3[C:16]([CH:17]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:18][CH2:19][O:20]3)=[CH:15][C:14]=2[Cl:28])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:28][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][C:13]=1[O:12][C:11]1[CH:29]=[CH:30][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=1)[O:20][CH2:19][CH2:18][CH:17]2[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080248Ethyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate

Product 1

HCID 582443954-(6-Chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate (8.62 g, 19.91 mmol) was diluted with DCM (40 ml) followed by the portion wise addition of TFA (30 ml). After stirring for 1 hour, the reaction was concentrated and placed under vacuum over the weekend. The residue was taken up in DCM and washed with saturated bicarbonate and 1N HCl. The organic layer was separated, dried over magnesium sulfate, filtered and concentrated to yield the desired compound (7.278 g, 19.32 mmol, 97.00% yield) as a nice white foam.

Workup

  1. concentrationthe reaction was concentrated
  2. washwashed with saturated bicarbonate and 1N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-90b37ead0ea343d5996ceacd6d352c4b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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