Dimethylformamide → 6-Bromo-2-naphthoyl chloride

HRID 724213Notes

Reaction equation

HRID 724213 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.S(Cl)([Cl:17])=O.CN(C=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([Cl:17])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796066-Bromo-2-naphthoyl chloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 6-bromo-2-naphthoic acid (100 g), thionyl chloride (37.7 ml) and DMF (0.5 ml) in THF (1000 ml) was stirred at 60° C. with heating for 90 min. After cooling to room temperature, the solvent was evaporated under reduced pressure. The resulting solid was dissolved in toluene and the solvent was evaporated to give 6-bromo-2-naphthoyl chloride as a pale yellow powder.

Workup

  1. temperaturewith heating for 90 min
  2. temperatureAfter cooling to room temperature
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionThe resulting solid was dissolved in toluene
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8467ed91b5ef477590f53d5db49c210d
Source dataset
uspto-grants-2006_11
Patent number
US07141598B2

Reaction notes

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