Dimethylformamide → 6-Bromo-2-naphthoyl chloride

HRID 1061878Notes

Reaction equation

HRID 1061878 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 with heating at 60° C. for 90 min. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The obtained solid was dissolved in toluene and the solvent was evaporated to give a pale-yellow powder of 6-bromo-2-naphthoyl chloride.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent was evaporated under reduced pressure
  3. dissolutionThe obtained solid was dissolved in toluene
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8f12ef396ac34b41b7677db2827a6db3
Source dataset
uspto-grants-2005_11
Patent number
US06960586B2

Reaction notes

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