2-Bromopropane → HCID 15341859, compound

HRID 347313Notes

Reaction equation

HRID 347313 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:20]([CH3:22])[CH3:21]>CN(C=O)C>[CH:20]([O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 5756094-bromonaphthalen-1-ol

Product 1

HCID 15341859HCID 15341859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The following is an adaptation of the method of Bringmann. A solution containing 4-bromo-1-naphthol (10.0 g, 0.045 mol), potassium carbonate (31 g, 0.224 mol), and 2-bromopropane (27.6 g, 0.224 mol) in DMF was heated at reflux for 1 h under a nitrogen atmosphere. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The resultant residue was subjected to silica gel chromatography using a 50% ethyl acetate-hexane mixture as the eluent to provide 4-isopropoxy-1-bromonaphthalene.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 h under a nitrogen atmosphere
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-01d2493deb9640a7997ae48e3838db92
Source dataset
uspto-grants-2007_02
Patent number
US07173134B2

Reaction notes

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