Benzyl Bromide → 6-Benzyloxynaphthalene-2-carboxylic acid methyl ester

HRID 550200Notes

Reaction equation

HRID 550200 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:15])[CH:11]=2)[CH:6]=1)=[O:4].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 390995Methyl 6-hydroxy-2-naphthoate

Product 1

HCID 199902746-Benzyloxynaphthalene-2-carboxylic acid methyl esterYield 83.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat 6-hydroxynaphthalene-2-carboxylic acid methyl ester (4.77 g, 23.6 μmmol) and benzyl bromide (3.3 mL, 28.3 mmol) in DMF (22 mL) with cesium carbonate (15.3 g, 47.2 mmol). Stir the mixture for 22 h at RT and concentrate. Dilute the concentrate with EtOAc (300 mL) and water (100 mL). Wash the organic layer with brine (3×100 mL), dry it over Na2SO4, and filter. Concentrate the filtrate. Purify the product using medium pressure silica gel chromatography (15:85 to 50:50 EtOAc:hex) to give the title compound as a white solid (5.75 g, 83%). MS (ES) m/e 293 (M+1).

Workup

  1. concentrationconcentrate
  2. additionDilute the
  3. concentrationconcentrate with EtOAc (300 mL) and water (100 mL)
  4. washWash the organic layer with brine (3×100 mL)
  5. dry with materialdry it over Na2SO4
  6. filtrationfilter
  7. concentrationConcentrate the filtrate
  8. customPurify the product

Sources & evidence

ORD record
ord-c4d07c329c584adab02045c7ffd89248
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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