1-Bromohexane → 2-Bromo-6-(hexyloxy)naphthalene

HRID 865859

Reaction equation

HRID 865859 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 45355832-Bromo-6-(hexyloxy)naphthaleneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of 4.46 g (20.0 mmol) of 6-bromo-2-naphthalenol (obtained from Aldrich Chemical Company (#B7,340-6) and used without purification), in 20 mL of DMF at room temperature under argon was added 480 mg (20 mmol) of 95% sodium hydride over the course of 15 min. The resulting light yellow solution was stirred 30 min and 3.5 mL (22 mmol) of 1-bromohexane was added. The reaction was heated to 50° C. and stirred for 60 min. The reaction was quenched with ice water, the resultings solids filtered, washed with water and dried in vacuo at 60° C. Purification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant) gave 5.00 g, 81% yield, of title compound as a colorless oil.

Workup

  1. stirringstirred for 60 min
  2. customThe reaction was quenched with ice water
  3. filtrationthe resultings solids filtered
  4. washwashed with water
  5. customdried in vacuo at 60° C
  6. customPurification of the residue by chromatography on silica gel (5×20 cm column, hexanes as elutant)
  7. customgave 5.00 g, 81% yield

Sources & evidence

ORD record
ord-366c43619d6748c8a70aa5bba187dba9
Source dataset
uspto-grants-1996_10
Patent number
US05567841

Linked notes

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