Bromine → HCID 67126247, compound

Reaction equation

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH3:12])[C:3]=1[C:13]#[N:14].C(=O)(O)[O-].[Na+].[Br:20]Br>C(Cl)(Cl)Cl>[Br:20][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([OH:1])=[C:3]([C:13]#[N:14])[C:4]=1[CH3:12]

Participants

Procedure

1-hydroxy-3-methyl-2-naphthonitrile (1.065 g, 5.8 mmol) was dissolved CHCl3 (24 mL) and combined with sodium bicarbonate (952 mg, 11.3 mmol) and bromine (330 μL, 6.43 mmol) and allowed to stir at room temperature overnight. The reaction was quenched by adding 10 mL of 10% sodium thiosulfate and the mixture stirred until decolorization was maximal. The solids were removed by filtration as crude product (1.47 g, 97% yield.) 1H-NMR: (300 MHz, DMSO-d6): δ 8.334 (d, J=8.0 Hz, 1H); 8.166 (d, J=8.4 Hz, 1H); 7.81-7.77 (m, 1H); 7.65-7.61 (m, 1H); 2.65 (s, 3H).