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

HRID 1771478Notes

Reaction equation

HRID 1771478 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.C1C(=O)N([Br:21])C(=O)C1.O>CN(C=O)C>[Br:21][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 962WaterHCID 67184N-bromobutanimideHCID 2886346-Methoxy-2-naphthol

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 6-methoxynaphthalen-2-ol (20 g, 114.8 mmol) in DMF (250 mL) was added a solution of NBS (21.5 g, 120 mmol) in DMF (50 mL) over a 30 min period. The reaction mixture was stirred for 45 min and poured into water. The precipitate was collected by filtration and dried to give the desired product (25.5 g, 87%) as white solid.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-63b4a7ffe3b34a98916dec1c2f43fbc5
Source dataset
uspto-grants-2016_02
Patent number
US09249132B2

Reaction notes

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