Trifluoroacetic acid → 4-(8-Bromo-6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid

HRID 510642Notes

Reaction equation

HRID 510642 reaction equation
[Br:1][C:2]1[C:3]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:21][CH:20]=2)=[C:4]([Cl:17])[CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13].FC(F)(F)C(O)=O>ClCCl>[Br:1][C:2]1[C:3]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:25]([OH:27])=[O:26])=[CH:23][CH:24]=2)=[C:4]([Cl:17])[CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67080441Ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate

Product 1

HCID 670804834-(8-Bromo-6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acidYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)phenoxy)-6-chlorochroman-4-carboxylate (0.26 g, 0.51 mmol) in dichloromethane (5 mL) at ambient temperature was added trifluoroacetic acid (5 mL). The resulting solution was stirred at ambient temperature for 30 minutes. The solution was concentrated and the residual glassy solid was redissolved in ethyl acetate (2 mL). Hexanes (10 mL) were added, and after mixing for a few minutes, the product solidified. The mixture was concentrated to afford 4-(8-bromo-6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid as a light brown powder (0.23 g, 99% yield).

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residual glassy solid was redissolved in ethyl acetate (2 mL)
  3. additionHexanes (10 mL) were added
  4. additionafter mixing for a few minutes
  5. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-edf008b9efe14f28b2f799b8b552ddb0
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

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