6-Bromo-2-naphthalenol → HCID 21883581, compound

HRID 1421600Notes

Reaction equation

HRID 1421600 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[Cl:13][C:14]1[C:15](F)=[CH:16][C:17]2[O:22][CH:21]([C:23]([F:26])([F:25])[F:24])[C:20]([C:27]([O:29]CC)=[O:28])=[CH:19][C:18]=2[CH:32]=1>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][C:15]1[C:14]([Cl:13])=[CH:32][C:18]3[CH:19]=[C:20]([C:27]([OH:29])=[O:28])[CH:21]([C:23]([F:25])([F:26])[F:24])[O:22][C:17]=3[CH:16]=1)[CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 271446-Bromo-2-naphthalenolHCID 21883602ethyl 6-chloro-7-fluoro-2-(trifluoromethyl)-2H-chromene-3-carboxylate

Product 1

HCID 21883581HCID 21883581, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was prepared from 6-bromo-2-napthol 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 252.6-254.8° C. 1H NMR (acetone-d/300 MHz) 8.19 (s, 1H), 8.04 (d, 1H, J=9.1 Hz), 7.93 (s, 1H), 7.87 (d, 1H, J=8.9 Hz), 7.75 (s, 1H), 7.65 (d, 1H, J=8.8 Hz), 7.55 (s, 1H), 7.43 (d, 1H, J=9.1 Hz), 6.72 (s, 1H), 5.83 (q, 1H, J=7.0 Hz). 19F NMR (acetone-d6 /282 MHz) -79.4 (d, J=6.5 Hz). FABLRMS m/z 497 (M-H). ESHRMS m/z 496.9421 (M-H, Calc'd 496.9403). Anal. Calc'd for C21H11BrClF3O4 with 1.75 wt % H2O: C, 49.60; H, 2.38; Br, 15.71; Cl, 6.97. Found: C, 49.55; H, 2.03; Br, 15.56; Cl, 7.22.

Sources & evidence

ORD record
ord-8a4e9c65ac9a4d55892b112c5845ae38
Source dataset
uspto-grants-2000_06
Patent number
US06077850

Reaction notes

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