Hydrochloric Acid → 6-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic Acid

HRID 854859Notes

Reaction equation

HRID 854859 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10](Cl)[C:11]=1O)[O:8][CH:7]([C:14]([F:17])([F:16])[F:15])[C:6]([C:18]([O:20]CC)=[O:19])=[CH:5]2.[OH-].[Li+].Cl>CO.C(#N)C.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][CH:7]([C:14]([F:17])([F:15])[F:16])[C:6]([C:18]([OH:20])=[O:19])=[CH:5]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69517486ethyl 6,8-dichloro-7-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 97956526-chloro-2-(trifluoromethyl)-2H-chromene-3-carboxylic AcidYield 70.5%

Reagents, catalysts & solvents 1

HCID 21864137Acetonitrile methanol waterSolvent

Procedure

A solution of the ester from Step 2 (0.20 g, 0.56 mmole) was dissolved in 3 mL mixture of MeOH/ACN/H2O=1/1/1, treated with lithium hydroxide (81 mg, 3.36 mmole) and stirred at room temperature for 2 days. The reaction mixture was acidified with 1.0 N HCl to pH=1 and was extracted with EtOAc. The organic layer was washed with water,dried over anhydrous MgSO4, and filtered. The filtrate was evaporated and dried in vacuo to afford the title compound as a yellow solid (0.11 g, 60%): ESHRMS m/z 326.9438 (M−H, C11H4O4F3Cl2, Calc'd 326.9433). 1H NMR (acetone-d6/400 MHz) 7.82 (s, 1H), 7.46(s, 1H), 6.00 (q, 1H, J=7.0 Hz).

Workup

  1. extractionwas extracted with EtOAc
  2. washThe organic layer was washed with water,dried over anhydrous MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3770f3cbda164067a85a93dcf4b83e9e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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