6-Bromonaphthalene-2-carbaldehyde → HCID 59270597, compound

HRID 446212Notes

Reaction equation

HRID 446212 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([CH:12]=O)[CH:6]=[CH:5]2.C([C:16](CC)(P(=O)([O-])[O-])[C:17]1[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=1)C.CC(C)([O-])C.[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7](/[CH:12]=[CH:16]/[C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=3)[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 134770296-Bromonaphthalene-2-carbaldehydeHCID 20474982HCID 20474982, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59270597HCID 59270597, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

6-bromo-2-naphthaldehyde (4.0 g, 17.1 mmol) and diethyl-4-bromobenzylphosphonate (6.3 g, 20.5 mmol) were dissolved in purified dimethylsulfoxide (100 mL) under a nitrogen atmosphere, the reaction solution was cooled down to 0° C., and then potassium t-butoxide (2.5 g, 20.5 mmol) was slowly added thereto. The reaction mixture solution was stirred at room temperature for 12 hours. The reaction mixture solution was subjected to extraction with water and dichloromethane to thereby remove the solvent. The extracted material was sufficiently washed with methanol, and was dried in vacuum to thereby obtain a white solid (6.0 g, yield: 91%).

Workup

  1. extractionThe reaction mixture solution was subjected to extraction with water and dichloromethane
  2. customto thereby remove the solvent
  3. washThe extracted material was sufficiently washed with methanol
  4. customwas dried in vacuum

Sources & evidence

ORD record
ord-fb7e95260cc24c3d97985c16466896d6
Source dataset
uspto-grants-2013_07
Patent number
US08476474B2

Reaction notes

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