Dimethylformamide → 1-Bromo-6-methoxynaphthalen-2-ol

HRID 445196Notes

Reaction equation

HRID 445196 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([OH:13])[CH:7]=[CH:6]2.CN(C)C=O.[Br:19]N1C(=O)CCC1=O>O>[Br:19][C:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:12][CH:11]=2)[CH:6]=[CH:7][C:8]=1[OH:13]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 2886346-Methoxy-2-naphthol

Product 1

HCID 184287461-Bromo-6-methoxynaphthalen-2-olYield 87.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add 6-methoxynaphthalene-2-ol (20 g, 114.8 mmol) to dimethylformamide (DMF, 250 mL) at ambient temperature followed by N-bromosuccinimide (NBS, 21.5 g, 120 mmol) over a 30 minute period. After 45 minutes, dilute with water (800 mL), collect and dry the precipitate to provide 25.5 g (87%) of 1-bromo-6-methoxy-naphthalen-2-ol.

Workup

  1. customcollect
  2. customdry the precipitate

Sources & evidence

ORD record
ord-8aa4e233586243f7807956e58ddde7ba
Source dataset
uspto-grants-2013_07
Patent number
US08476300B2

Reaction notes

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