Bromine → HCID 67126247, compound

HRID 514139Notes

Reaction equation

HRID 514139 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

5

Reactant 3

HCID 24408BromineHCID 2193751-hydroxy-3-methylnaphthalene-2-carbonitrileHCID 516892Sodium Bicarbonate

Product 1

HCID 67126247HCID 67126247, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

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).

Workup

  1. customThe reaction was quenched
  2. additionby adding 10 mL of 10% sodium thiosulfate
  3. stirringthe mixture stirred until decolorization

Sources & evidence

ORD record
ord-59074cc183fe4f9089eeb08d49cb9fd8
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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