Hydrofluoric Acid → 7-(1,1-Dimethylethyl)-2-trifluoromethyl-2h-1-benzopyran-3-carboxylic acid

HRID 1421562Notes

Reaction equation

HRID 1421562 reaction equation
[CH3:1][C:2]([C:5]1[CH:23]=[CH:22][C:8]2[CH:9]=[C:10]([C:17]([O:19]CC)=[O:18])[CH:11]([C:13]([F:16])([F:15])[F:14])[O:12][C:7]=2[CH:6]=1)([CH3:4])[CH3:3].F>>[CH3:4][C:2]([C:5]1[CH:23]=[CH:22][C:8]2[CH:9]=[C:10]([C:17]([OH:19])=[O:18])[CH:11]([C:13]([F:14])([F:15])[F:16])[O:12][C:7]=2[CH:6]=1)([CH3:1])[CH3:3]

Participants

3

Reactant 2

HCID 14917Hydrofluoric AcidHCID 21883685Ethyl 7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2h-1-benzopyran-3-carboxylate

Product 1

HCID 99044067-(1,1-Dimethylethyl)-2-trifluoromethyl-2h-1-benzopyran-3-carboxylic acid

Procedure

Ethyl 7-(1,1-dimethylethyl)-2-(trifluoromethyl)-2H-1-benzopyran-3-carboxylate (Example 8, Step 2) was hydrolyzed to the carboxylic acid is a procedure similar to that described in Example 1, Step 2: mp 165.6-166.8° C. 1H NMR (acetone-d6 /300 MHz) 7.86 (s, 1H), 7.38 (d, 1H, J=8.1 Hz), 7.1) (dd, 1H, J=1.8 Hz, and J=7.8 Hz), 7.05 (bs, 1H), 5.79 (q H-F, 1H, J=7.2 Hz), 1.32 (s, 9H). FABHRMS m/z 301.1033 (M+H, Calc'd 301.1051). Anal. Calc'd for C15H15F3O3 : C, 60.00; H, 5.04. Found: C, 59.80; H, 5.10.

Sources & evidence

ORD record
ord-5ca91a5fdd8546ada5857e518a0f2f07
Source dataset
uspto-grants-2000_06
Patent number
US06077850

Reaction notes

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