Benzyl Bromide → HCID 14520029, compound

HRID 1607769Notes

Reaction equation

HRID 1607769 reaction equation
C(S)CC.[H-].[Na+].[CH3:7][O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[CH:21]=[O:22].C([O-])([O-])=O.[K+].[K+].C(Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O>[CH3:20][O:19][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[C:10]([CH:21]=[O:22])=[C:9]([O:8][CH2:7][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH:18]=[CH:17]2

Participants

7

Reactant 5

HCID 7498Benzyl BromideHCID 7848Propyl mercaptanHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 12583354HCID 12583354, compound

Product 1

HCID 14520029HCID 14520029, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Propanethiol (12.8 mL, 0.141 mol) was added over a 20 minute period to a suspension of sodium hydride (2.92 g, 0.122 mol) in N,N-dimethylformamide at 0° C. under a nitrogen atmosphere. To the resulting solution was added a solution of 2,6-dimethoxy-1-naphthalenecarboxaldehyde [21.6 g, 0.100 mol, described by N. P. Buu-Hoi et al, J. Chem. Soc., 2776 (1955)] in 100 mL of N,N-dimethylformamide, and the mixture was heated at 50°-60° C. for 3 hours. Anhydrous K2CO3 (28 g, 0.20 mol) and benzyl bromide (28.6 mL, 0.24 mol) were added and heating was continued for 2 hours. The mixture was cooled to room temperature overnight, then concentrated under vacuum. The residue was dissolved in water (800 mL) and ethyl acetate (1 L). The organic phase was collected and washed successively with 1M KOH, (400 mL), water (200 mL), and saturated NaCl and then dried over Na2SO4. After filtration and evaporation of the solvent, the residue was recrystallized from absolute ethanol to give 19.6 g, of the title compound as a yellow solid, m.p. 115°-117° C.

Workup

  1. temperaturethe mixture was heated at 50°-60° C. for 3 hours
  2. temperatureheating
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in water (800 mL)
  5. customThe organic phase was collected
  6. washwashed successively with 1M KOH, (400 mL), water (200 mL), and saturated NaCl
  7. dry with materialdried over Na2SO4
  8. filtrationAfter filtration and evaporation of the solvent
  9. customthe residue was recrystallized from absolute ethanol
  10. customto give 19.6 g

Sources & evidence

ORD record
ord-95799ef27a9949ed80b82841915788cc
Source dataset
uspto-grants-1989_09
Patent number
US04866197

Reaction notes

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