Benzyl Bromide → HCID 68838619, compound

HRID 2110568Notes

Reaction equation

HRID 2110568 reaction equation
[In].[CH2:2](Br)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH:10][C:11]1[C:12](=[O:22])[C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[Cl-].[NH4+].C([O-])(=O)C(C(C([O-])=O)O)O.[K+].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:2]([C:12]1([OH:22])[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]([OH:21])=[CH:20][C:11]1=[O:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 7498Benzyl BromideHCID 25517Ammonium ChlorideHCID 5359967Indium2×HCID 9855836Potassium sodium tartarateHCID 178516607HCID 178516607, compound

Product 1

HCID 68838619HCID 68838619, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of indium powder (529 mg, 4.60 mmol) in anhydrous N,N-dimethylformamide (4.6 mL) at 25° C. was treated dropwise with benzyl bromide (1.18 g, 820 μL, 6.90 mmol). After addition, the mixture became warm, and after stirring for 2 h, most of the indium was consumed. The solution was cooled to 0° C. and a cold (0° C.) solution of 2-hydroxy-1,4-naphthoquinone (200 mg, 1.15 mmol) in N,N-dimethylformamide (2 mL) was added via cannula. The orange solution was stirred at 0° C. for 3 h, and then allowed to warm to ambient temperature for 18 h. The pale yellow solution was treated with saturated ammonium chloride solution and diluted with ethyl acetate. The mixture was stirred with saturated sodium potassium tartarate solution until most solids had dissolved. The layers were separated and the organic layer was extracted with water (4×) and saturated NaCl solution. Drying (Na2SO4), filtering and concentration in vacuo afforded an oil, which was purified by flash chromatography, eluting with methanol in dichloromethane. These procedures afforded the title compound (181 mg, 68%) as a light yellow oil. 1H NMR (300 MHz, CDCl3): δ 8.10-6.75 (m, 9H), 4.70 (s, 2H), 4.15 (s, 1H), 3.85 (d, J=19.12 Hz, 1H), 3.70 (d, J=19.12 Hz, 1H).

Workup

  1. additionAfter addition
  2. temperaturethe mixture became warm
  3. customwas consumed
  4. temperatureto warm to ambient temperature for 18 h
  5. dissolutionhad dissolved
  6. customThe layers were separated
  7. extractionthe organic layer was extracted with water (4×) and saturated NaCl solution
  8. dry with materialDrying (Na2SO4)
  9. filtrationfiltering
  10. concentrationconcentration in vacuo
  11. customafforded an oil, which
  12. customwas purified by flash chromatography
  13. washeluting with methanol in dichloromethane

Sources & evidence

ORD record
ord-4502cdc9e8484ea48fbd79e91f45e360
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

Loading…