Benzyl Bromide → HCID 18519025, compound

HRID 1369279Notes

Reaction equation

HRID 1369279 reaction equation
[CH:1]([C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:14]([OH:16])=[O:15])=[CH:8]2)=[O:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH:1]([C:3]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])=[CH:8]2)=[O:2]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 133969875-Formyl-6-hydroxynaphthalene-2-carboxylic acid

Product 1

HCID 18519025HCID 18519025, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-formyl-6-hydroxy-2-naphthoic acid (1.12 g, 5.18 mmol) in 7.3 mL DMF at rt under N2 was added 569 mg (5.69 mmol) of KHCO3 and 1.11 mL (9.32 mmol) of benzyl bromide. The mixture was stirred for 3 days, at which point it was diluted with H2O and extracted with EtOAc. The extract was washed with saturated aqueous NaHCO3, dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography on silica gel, using 85:15 hexanes-EtOAc as the eluent, to give 410 mg (25%).

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with saturated aqueous NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography on silica gel
  6. customto give 410 mg (25%)

Sources & evidence

ORD record
ord-ccf38b3c32bd4b1aa4d397a1c588bcd2
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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