Water → 2-[(3-Bromophenoxy)methyl]naphthalene

HRID 1741168Notes

Reaction equation

HRID 1741168 reaction equation
Br[CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[Br:19][C:20]1[CH:21]=[C:22]([OH:26])[CH:23]=[CH:24][CH:25]=1.O>CN(C=O)C>[Br:19][C:20]1[CH:21]=[C:22]([CH:23]=[CH:24][CH:25]=1)[O:26][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 115633-BromophenolHCID 703202-Bromomethylnaphthalene

Product 1

HCID 150499662-[(3-Bromophenoxy)methyl]naphthaleneYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyinaphthalene (5.00 g, 22.6 mmol) was dissolved in N,N'-dimethylformamide (100 ml) and potassium carbonate (9.4 g, 68 mmol) and 3-bromophenol (3.91 g, 22.6 mmol) were added. The mixture was stirred vigorously for 16 h at room temperature and then poured into water (700 ml). The precipitate was filtered off, washed with water and dried in vacuo at 50° C. for 16 h to give 6.17 g (87%) of 2-(3-bromophenoxymethyl)naphthalene as a solid.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with water
  3. customdried in vacuo at 50° C. for 16 h

Sources & evidence

ORD record
ord-90e48017b71044ae846eb131c24e1712
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

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