Tetrahydrofuran → 6-Bromo-2-naphthalenecarboxylic acid

HRID 2359998Notes

Reaction equation

HRID 2359998 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]([O:14]C)=[O:13])[CH:6]=[CH:5]2.C1COCC1.O.[OH-].[Li+]>O>[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:13])[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 8541342-Bromo-6-methoxycarbonylnaphthalene

Product 1

HCID 45498526-Bromo-2-naphthalenecarboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of methyl 6-bromo-2-naphthoate (7.70 g, 29.0 mmol) in 2:1 THF:water (150 mL) was treated with lithium hydroxide hydrate (2.44 g, 58.1 mmol) followed by stirring at room temperature for 48 h. Concentrated under vacuum, diluted with water and cooled to 0° C. Acidified to pH3 with 4N HCl. Solids were collected by filtration, dissolved in toluene-EtOAc (ca. 2 L) and washed with brine. Dried over Na2SO4, filtered and concentrated under vacuum. Brown solid was triturated with ether, collected by filtration, and dried under vacuum to give the title compound as a nearly white solid (5.07 g, 70%).

Workup

  1. concentrationConcentrated under vacuum
  2. additiondiluted with water
  3. temperaturecooled to 0° C
  4. filtrationSolids were collected by filtration
  5. dissolutiondissolved in toluene-EtOAc (ca. 2 L)
  6. washwashed with brine
  7. dry with materialDried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customBrown solid was triturated with ether
  11. filtrationcollected by filtration
  12. customdried under vacuum

Sources & evidence

ORD record
ord-0095a11048a8433ca2c9d372f4ee0538
Source dataset
uspto-grants-2014_04
Patent number
US08685991B2

Reaction notes

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