Hydrochloric Acid → 6-chloro-7-(2-chloro-4,5-dimethylphenoxy)-2-(trifluoromethyl)-2H-chromene-3-carboxylic acid

HRID 855006Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:25])([F:24])[F:23])[C:6]([C:26]([O:28]CC)=[O:27])=[CH:5]2.O.[OH-].[Li+].[Al].Cl>C(OCC)C.C1COCC1.CO.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH3:20])=[CH:15][C:14]=1[Cl:21])[O:8][CH:7]([C:22]([F:24])([F:25])[F:23])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

To the concd product of step 1 in a suitable vial was added 400 mg (mmole) of lithium hydroxide monohydrate, 1 mL of water, 2 mL of methanol and 7 mL of THF. The vial was capped, in an aluminum heating block and the block heated to 100° C. for 30 min. After allowing the vial to cool to rt, the mixture was treated with 5 mL of 1N HCl and 2 mL of diethyl ether. The organic layer was removed and the aqueous layer extracted two times with diethyl ether. Combined organic extracts were concd by evaporation of solvent under a stream of N2 followed by conc in vacuo to afford 150 mg (34.6%) of a yellow solid: 1H NMR (CDCl3/300 MHz) 2.26 (s, 3H), 5.64 (q, 1H, J=6.8 Hz), 6.27 (s, 1H), 6.94 (s, 1H), 7.26 (s, 1H), 7.3H (s, 1H), 11.28 (hs, 1H); MS (ES−) 431 (M−1, 100); HRMS (ES−) m/z calcd for (M−H; C19H12Cl2F3O4) 431.0059, found 431.0048.

Workup

temperatureto cool to rt
customThe organic layer was removed
extractionthe aqueous layer extracted two times with diethyl ether
customCombined organic extracts were concd by evaporation of solvent under a stream of N2

Sources & evidence

ORD record: ord-f034ea96a5b345dea9a765ca46c4cf98
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259266B2

Reaction notes

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