Benzyl Bromide → HCID 59685145, compound

HRID 899431Notes

Reaction equation

HRID 899431 reaction equation
C(O[C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[C:9]([Br:15])[C:8]=1[OH:16])C.C([O-])([O-])=O.[K+].[K+].C(Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C.CCOC(C)=O>[CH2:14]([O:13][C:11]1[CH:12]=[C:7]2[C:8](=[C:9]([Br:15])[CH:10]=1)[O:16][C:4](=[O:17])[CH:5]=[CH:6]2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 59685154HCID 59685154, compound

Product 1

HCID 59685145HCID 59685145, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Dissolve preparation 2 (66.5 g, 275.89 mmol) in 1.5 L of dry DMF. Add finely powdered (325 mesh) K2CO3 (91.56 g, 662.13 mmol) followed by benzyl bromide (56.63 g, 331.07 mmol). Stir rapidly at room temperature overnight. Add 2 L of EtOAc, wash with H2O (1×2 L), 10% LiCl (3×, 4 L total volume) and brine. Dry over Na2SO4, filter and civ to yield a brown solid. Dissolve in hot EtOAc (2 L), filter off an insoluble brown solid, add hexane (˜500 mL) and allow to cool slowly, overnight. Filter off the resultant brown solid. This yields 50.3 g of a dark brown material. A second crop crashes out of the filtrate. This yields 8.1 g of a tan solid. Reduce the filtrate volume to ˜500 mL and placed on a plug of silica gel (1 kg, eluted with 1:1 EtOAc/hexane) to yield an additional 14.9 g of a darker brown solid. The total combined yield is 73.3 g (80%) of preparation 3. NMR (DMSO-d6) δ 7.96 (d, J=9.2 Hz, 1H), 7.58 (d, J=2.6 Hz, 1H), 7.45-7.32 (m, 6H), 6.53 (d, J=9.7 Hz, 1H), 5.15 (s, 2H).

Workup

  1. dissolutionDissolve
  2. additionAdd finely
  3. washwash with H2O (1×2 L), 10% LiCl (3×, 4 L total volume) and brine
  4. dry with materialDry over Na2SO4
  5. filtrationfilter
  6. customciv to yield a brown solid
  7. filtrationfilter off an insoluble brown solid
  8. additionadd hexane (˜500 mL)
  9. temperatureto cool slowly, overnight
  10. filtrationFilter off the resultant brown solid

Sources & evidence

ORD record
ord-de49c49da1144dc28cd1baa2d618037a
Source dataset
uspto-grants-2008_04
Patent number
US07354951B2

Reaction notes

Loading…