Water → 3-Bromo-8-chloro-7-hydroxy-1-naphthonitrile
Reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([C:12]#[N:13])=[CH:9][CH:8]=[CH:7]2.[Br:15]Br.O>C(O)(=O)C>[Br:15][C:8]1[CH:9]=[C:10]([C:12]#[N:13])[C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]([OH:14])[C:2]=2[Cl:1]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a mixture of 8-chloro-7-hydroxy-1-naphthonitrile (0.127 g, 0.63 mmol) and glacial acetic acid (1 mL) in a pressure tube was added a solution of bromine (0.24 g, 1.5 mmol) in glacial acetic acid (2 mL). The tube was sealed and the mixture was stirred at 100° C. overnight. The reaction was cooled, poured into water (50 mL), and extracted with ethyl acetate (3×100 mL). The combined organic layers were washed with sodium bicarbonate solution, dried over sodium sulfate, filtered, stripped of solvent, and purified on a silica column (20% ethyl acetate—hexanes) to yield 0.10 g (56%) of the title compound as a yellow solid. An analytical sample was prepared by preparative reverse phase HPLC to yield the title compound as a white solid: mp 148-150° C.; 1H NMR (DMSO-d6): δ 7.47 (1H, d, J=8.98 Hz), 7.95 (1H, d, J=9.02 Hz), 8.32 (1H, d, J=2.08 Hz), 8.55 (1H, d, J=2.08 Hz), 11.33 (1H, s); MS (ESI) m/z 280/282/284 (M−H)−.
Workup
- customThe tube was sealed
- temperatureThe reaction was cooled
- extractionextracted with ethyl acetate (3×100 mL)
- washThe combined organic layers were washed with sodium bicarbonate solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- custompurified on a silica column (20% ethyl acetate—hexanes)
Sources & evidence
- ORD record
- ord-01373bdda6674021a03d64bca0324a57
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06914074B2
Reaction notes
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