Oxalyl chloride → 6-Bromo-2-naphthoyl chloride

HRID 1486397Notes

Reaction equation

HRID 1486397 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.C(Cl)(=O)C([Cl:18])=O>ClCCl.CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([Cl:18])=[O:14])[CH:6]=[CH:5]2

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 45498526-Bromo-2-naphthalenecarboxylic acid

Product 1

HCID 218796066-Bromo-2-naphthoyl chlorideYield 100.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

6-bromo-2-naphthoic acid (72.3 g, 282 mmol, 1.0 equiv.) was suspended in dichloromethane (600 mL) and DMF (catalytic, 5 drops) was added. Oxalylchloride (71.6 g, 564 mmol, 2.0 equiv.) was added portion wise during 1 hour. The reaction mixture was stirred overnight with a CaCl2 drying tube mouthed on the flask. Complete dissolution occurred. The reaction mixture was concentrated, dichloromethane (100 mL) was added and the solvent was evaporated again, yielding 6-bromo-2-naphthoyl chloride (76.1 g, 100%) as an oil which was used as such in next step.

Workup

  1. dissolutionComplete dissolution
  2. concentrationThe reaction mixture was concentrated
  3. additiondichloromethane (100 mL) was added
  4. customthe solvent was evaporated again

Sources & evidence

ORD record
ord-ea6aec3bedfe46b59afa6639e7d5f164
Source dataset
uspto-grants-2016_08
Patent number
US09427428B2

Reaction notes

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