Dimethylformamide → 2-bromo-6-butoxynaphthalene

HRID 1194500Notes

Reaction equation

HRID 1194500 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([OH:14])[CH:8]=[CH:7]2.I[CH2:16][CH2:17][CH2:18][CH3:19].CN(C=O)C>C1COCC1.O>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:16][CH2:17][CH2:18][CH3:19])[CH:10]=2)[CH:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 271446-Bromo-2-naphthalenol

Product 1

HCID 37984142-bromo-6-butoxynaphthaleneYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

An oil dispersion of 480 mg (50%, 10 mmol, Alfa) of sodium hydride was washed three times with petroleum ether then the residue covered with 5 ml of dry THF. To the resulting stirred slurry was added dropwise a solution of 2.00 g (8.97 mmol, Aldrich) of 6-bromo-2-naphthol, in 10 ml of THF over 10 minutes. The reaction mixture was stirred for 30 minutes then 1.70 g (9.23 mmol, Aldrich) of 1-iodobutane and 15 ml of sieve-dried DMF were added. The resulting solution was heated to 60° for two hours, then cooled, added to 100 ml of H2O and extracted with 50 ml of petroleum ether. The organic extract was washed with an additional 100 ml of H2O, dried (MgSO4) and concentrated in vacuo to give a solid. The crude material was purified by flash chromatography (15×5 cm, pet ether) to afford 2.31 g (92%) of title compound as a white solid, m.p. 48°-50°.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. temperatureThe resulting solution was heated to 60° for two hours
  3. temperaturecooled
  4. extractionextracted with 50 ml of petroleum ether
  5. extractionThe organic extract
  6. washwas washed with an additional 100 ml of H2O
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give a solid
  10. customThe crude material was purified by flash chromatography (15×5 cm, pet ether)

Sources & evidence

ORD record
ord-4d7158b182a14df1bad8df24ef7745ba
Source dataset
uspto-grants-1989_03
Patent number
US04814454

Reaction notes

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