Potassium Carbonate → HCID 21883499, compound

HRID 650196Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].[Cl:12][C:13]1[C:14](F)=[CH:15][C:16]2[O:21][CH:20]([C:22]([F:25])([F:24])[F:23])[C:19]([C:26]([O:28]CC)=[O:27])=[CH:18][C:17]=2[CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>>[C:5]([C:4]1[CH:8]=[CH:9][C:10]([O:11][C:14]2[C:13]([Cl:12])=[CH:31][C:17]3[CH:18]=[C:19]([C:26]([OH:28])=[O:27])[CH:20]([C:22]([F:24])([F:25])[F:23])[O:21][C:16]=3[CH:15]=2)=[C:2]([Cl:1])[CH:3]=1)([OH:7])=[O:6]

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 198603-Chloro-4-hydroxybenzoic acid

HCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 21883499HCID 21883499, compound

Procedure

The title compound was prepared from 3-chloro-4-hydroxybenzoic acid and ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (Example 183, Step 2) via a procedure similar to that described in Example 183, Steps 3 and 4. (Note: In the step similar to Example 183, Step 3, an additional equivalent of potassium carbonate was added.) mp >300° C. 1H NMR (acetone-d6/300 MHz) 8.18 (d, 1H, J=2.0 Hz), 8.03 (dd, 1H, J=8.5 Hz 2.0 Hz), 7.93 (s, 1H), 7.78 (s, 1H), 7.23 (d, 1H, J=8.7 Hz), 6.77 (s, 1H), 5.87 (q, 1H, J=7.0 Hz). 19F NMR (acetone-d6/282 MHz) −79.4 (d, J=6.5 Hz). ESHRMS m/z 446.9625 (M−H, Calc'd 446.9650). Anal. Calc'd for C18H9Cl2F3O6: C, 48.13; H, 2.02 ; Cl, 15.79. Found: C, 47.96; H, 1.90; Cl, 15.65.

Sources & evidence

ORD record: ord-50cb5a9997144369ae76c368d51e1e36
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271253B1

Reaction notes

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