Trifluoroacetic acid → 4-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

HRID 1626500Notes

Reaction equation

HRID 1626500 reaction equation
C([O:5][C:6]([C:8]1[CH:31]=[CH:30][C:11]([O:12][C:13]2[C:22]([Cl:23])=[C:21]3[C:16]([CH:17]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:18][CH2:19][O:20]3)=[CH:15][C:14]=2[Cl:29])=[CH:10][CH:9]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:29][C:14]1[CH:15]=[C:16]2[C:21](=[C:22]([Cl:23])[C:13]=1[O:12][C:11]1[CH:30]=[CH:31][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=1)[O:20][CH2:19][CH2:18][CH:17]2[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080347Ethyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6,8-dichlorochroman-4-carboxylate

Product 1

HCID 670803034-(6,8-Dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidYield 113.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 7-(4-(tert-butoxycarbonyl)phenoxy)-6,8-dichlorochroman-4-carboxylate (1.85 g, 3.96 mmol) in 20 mL of DCM was added trifluoroacetic acid (10 mL). After stirring at ambient temperature for 1 hour, the mixture was concentrated to a sticky residue. The residue was dissolved in ethyl acetate and washed successively with saturated sodium bicarbonate and brine. The solution was then dried over sodium sulfate and filtered. The filtrate was concentrated to give the desired product (1.85 g, 90.9% yield) as a powder.

Workup

  1. concentrationthe mixture was concentrated to a sticky residue
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed successively with saturated sodium bicarbonate and brine
  4. dry with materialThe solution was then dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0e8a66eb46d24f11ae08860d2d23eb52
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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