Water → 4-Bromo-1-naphthaldehyde

HRID 388367Notes

Reaction equation

HRID 388367 reaction equation
[C:1](=[O:4])(O)[O-].[Na+].[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10](CBr)=[CH:9][CH:8]=1.O>CS(C)=O>[Br:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:1]=[O:4])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 127491471-Bromo-4-(bromomethyl)naphthalene

Product 1

HCID 46404134-Bromo-1-naphthaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

Sodium bicarbonate (1.4 g) is added to a solution of crude 1-bromo-4-bromomethyl-naphthalene (2.5 g) in DMSO (25 ml). The reaction is stirred for 3 h at 95° C. and cooled down to room temperature. Water is added and the mixture is extracted with ethyl acetate. The organic phase is dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 4-bromo-naphthalene-1-carbaldehyde as colorless crystals.

Workup

  1. temperaturecooled down to room temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-554be38d43774d25bd92901008251605
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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