Benzyl Bromide → HCID 58493293, compound

HRID 1518929Notes

Reaction equation

HRID 1518929 reaction equation
[F:1][C:2]1[C:3]([CH3:21])=[C:4]([C:14]([OH:20])=[C:15]([N+:17]([O-:19])=[O:18])[CH:16]=1)[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6].C([O-])([O-])=O.[K+].[K+].[CH:28]1[CH:33]=[CH:32][C:31]([CH2:34]Br)=[CH:30][CH:29]=1>CC(C)=O>[CH2:34]([O:20][C:14]1[C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:2]([F:1])=[C:3]([CH3:21])[C:4]=1[C:5]([O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6])[C:31]1[CH:32]=[CH:33][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58493235HCID 58493235, compound

Product 1

HCID 58493293HCID 58493293, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 30 L 4-neck flask equipped with mechanical stirrer, thermometer, addition funnel and gas inlet was charged with a solution of compound 64 (1423 g, 4.89 mol) in acetone (17 L). K2CO3 (1350 g, 9.8 mol) and KI (81 g, 0.49 mol) were added to the stirring reaction mixture and the resulting suspension was degassed with N2 for 5 min prior to adding BnBr (878.2 g, 5.13 mol) at 27˜29° C. over 8 mM. After the addition, the brown suspension was refluxed for 2.5 h, then allowed to cool to 20˜30° C. The suspension was filtered, and the filter cake was washed with acetone (3×900 mL). The filtrate was concentrated under reduced pressure and the residual oil was dissolved in MTBE (7.0 L) and successively washed with water (5×1.0 L) and brine (4×1.0 L). The organic layer was dried over Na2SO4 filtered then concentrated to dryness under reduced pressure to afford 1840 g of crude compound 65 (98.7% yield) as brown oil.

Workup

  1. customA 30 L 4-neck flask equipped with mechanical stirrer
  2. additionthermometer, addition funnel and gas inlet
  3. customthe resulting suspension was degassed with N2 for 5 min
  4. additionAfter the addition
  5. temperaturethe brown suspension was refluxed for 2.5 h
  6. temperatureto cool to 20˜30° C
  7. filtrationThe suspension was filtered
  8. washthe filter cake was washed with acetone (3×900 mL)
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. dissolutionthe residual oil was dissolved in MTBE (7.0 L)
  11. washsuccessively washed with water (5×1.0 L) and brine (4×1.0 L)
  12. dry with materialThe organic layer was dried over Na2SO4
  13. filtrationfiltered
  14. concentrationthen concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-3a8ba863a5ea4b9987ae316945496acc
Source dataset
uspto-grants-2015_07
Patent number
US09073829B2

Reaction notes

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