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

HRID 1626372Notes

Reaction equation

HRID 1626372 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 dried over sodium sulfate and filtered. The filtrate was concentrated to give 4-(6,8-dichloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (1.85 g, 90.9% yield) as a powder. 1H NMR (400 MHz, CDCl3) δ 8.07 (d, J=8.8 Hz, 2H), 7.35 (s, 1H), 6.90 (d, J=8.8 Hz, 1H), 4.36-4.48 (m, 2H), 4.25 (q, J=7.1 Hz, 2H), 3.80 (t, J=4.7 Hz, 1H), 2.37-2.43 (m, 1H), 2.11-2.20 (m, 1H), 1.32 (t, J=7.2 Hz, 3H).

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 dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-223d9e5e9f55478a89f882d3800d002b
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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