Hydrochloric Acid → 5-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855137Notes

Reaction equation

HRID 855137 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:16]([O:18]CC)=[O:17])[CH:6]([C:12]([F:15])([F:14])[F:13])[O:7]2.[OH-].[Li+].Cl>C1COCC1.CO.O>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:16]([OH:18])=[O:17])[CH:6]([C:12]([F:15])([F:14])[F:13])[O:7]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58934554ethyl 5-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 589344605-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylic acidYield 80,104.602%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 290 mg (1.0 mmole) of ethyl 5-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate in 7 mLs of THF and 2 mL of methanol was added a solution of 85 mg of lithium hydroxide monohydate in 1.0 mL of water. The mixture was heated to reflux for 30 min and allowed to cool to rt. After stirring overnight, the mixture was treated with 75 mL of 1N HCl and extracted three times with diethyl ether. The combined extracts were washed with brine, dried and concd in vacuo to afford 210 g (80%) of a white solid: 1H NMR (d6-acetone/400 MHz) 5.86 (q, 1H, J=7.1 Hz), 6.88 (m, 2H), 7.44 (q, 1H, J=6.7 Hz), 7.93 (s, 1H); 19F NMR (d6-acetone/400 MHz) −120.9 (t, 1F, J=7.7 Hz), −79.4 (d, 3F, J=7.7 Hz); MS (ES+) 263 (M+l, 100); MS (ES−) 261 (M−1, 100); HRMS (ES−) m/z calcd for (C11H6F4O3) 261.0175, found 261.0193.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 30 min
  3. extractionextracted three times with diethyl ether
  4. washThe combined extracts were washed with brine
  5. customdried

Sources & evidence

ORD record
ord-118905b1b4294787bde190b3c6a3fd8e
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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