2-Bromo-4-chlorophenol → HCID 21883543, compound

HRID 2297901Notes

Reaction equation

HRID 2297901 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Cl:10][C:11]1[C:12](F)=[CH:13][C:14]2[O:19][CH:18]([C:20]([F:23])([F:22])[F:21])[C:17]([C:24]([O:26]CC)=[O:25])=[CH:16][C:15]=2[CH:29]=1>>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[O:9][C:12]1[C:11]([Cl:10])=[CH:29][C:15]2[CH:16]=[C:17]([C:24]([OH:26])=[O:25])[CH:18]([C:20]([F:22])([F:23])[F:21])[O:19][C:14]=2[CH:13]=1

Participants

3

Reactant 2

HCID 696702-Bromo-4-chlorophenolHCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 21883543HCID 21883543, compound

Procedure

The title compound was prepared from 2-bromo-4-chlorophenol 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: mp 223.6-225.6° C. 1H NMR (acetone-d6/300 MHz) 7.89 (s, 1H), 7.83 (d, 1H, J=2.6 Hz), 7.73 (s, 1H), 7.52 (dd, 1H, J=8.7 Hz, 2.4 Hz), 7.25 (d, 1H, J=8.9 Hz), 6.55 (s, 1H), 5.83 (q, 1H, J=7.0 Hz). 19F NMR (acetone-d6/282 MHz)−79.4 (d, J=7.2 Hz). FABLRMS m/z 481 (M−H). ESHRMS m/z 480.8856 (M−H, Calc'd 480.8857). Anal. Calc'd for C17H8BrCl2F3O4: C, 42.18; H, 1.67; Br, 16.51; Cl, 14.65. Found: C, 42.15; H, 1.54; Br, 16.56; Cl, 14.39.

Sources & evidence

ORD record
ord-0e26b61d14714e15b78a8615c5fbefd4
Source dataset
uspto-grants-2002_12
Patent number
US06492390B2

Reaction notes

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