Methanol → Methyl 5-bromo-1-naphthoate

HRID 1276285

Reaction equation

HRID 1276285 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([OH:14])=[O:13].S(Cl)(Cl)=O.[CH3:19]O>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]([O:14][CH3:19])=[O:13]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 6976055-Bromonaphthalene-1-carboxylic acid

Product 1

HCID 4557673Methyl 5-bromo-1-naphthoateYield 98%

Procedure

5-Bromonapthoic acid (J Chem. Soc., 1950, 991) (5.13 g, 20 mmol) was added to a solution of thionyl chloride (10 ml) in methanol (200 ml). The mixture was stirred at reflux for 4 h, yielding a dark brown solution. On cooling, the title compound precipitated as a light brown solid, which was filtered off and dried, yielding 5.34 g material (98%).

Workup

  1. temperatureat reflux for 4 h
  2. customyielding a dark brown solution
  3. temperatureOn cooling
  4. customthe title compound precipitated as a light brown solid, which
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-0544a106c9df4ab4803927fdf110d11e
Source dataset
uspto-grants-2000_12
Patent number
US06166034

Linked notes

Loading…