Benzyl Bromide → Methyl 7-(benzyloxy)naphthalene-2-carboxylate

HRID 550213Notes

Reaction equation

HRID 550213 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][C:9]([OH:15])=[CH:10][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][C:9]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:10][CH:11]=2)[CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 10081555METHYL 7-HYDROXY-2-NAPHTHOATE

Product 1

HCID 53429438Methyl 7-(benzyloxy)naphthalene-2-carboxylateYield 36%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treat a solution of 7-hydroxynaphthalene-2-carboxylic acid methyl ester (2.84 g, 14.0 mmol) and benzyl bromide (1.84 mL, 15.5 mmol in DMF (14 mL) with cesium carbonate (9.10 g, 27.9 mmol). Stir the mixture for 2 h and concentrate. Dissolve the crude residue in EtOAc (150 mL) and 1 N HCl (50 mL). Wash the organic layer with brine (3×100 mL), dry over Na2SO4, and filter. Concentrate the filtrate and purify using medium pressure silica gel chromatography (10:90 EtOAc:hex) to give the title compound as a white solid (1.47 g, 36%). MS (ES) m/e 293 (M+1).

Workup

  1. concentrationconcentrate
  2. dissolutionDissolve the crude residue in EtOAc (150 mL) and 1 N HCl (50 mL)
  3. washWash the organic layer with brine (3×100 mL)
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationConcentrate the filtrate
  7. custompurify

Sources & evidence

ORD record
ord-b763b132b2914ec495a0497b20d5005e
Source dataset
uspto-grants-2011_05
Patent number
US07943795B2

Reaction notes

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