Benzyl Bromide → HCID 86638340, compound

HRID 2390804Notes

Reaction equation

HRID 2390804 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:14]2[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=2)[C:8]([OH:13])=[C:9]([CH:12]=1)[CH:10]=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:22]([O:13][C:8]1[C:7]([C:14]2[C:15]([O:20][CH3:21])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:12][C:9]=1[CH:10]=[O:11])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86638339HCID 86638339, compound

Product 1

HCID 86638340HCID 86638340, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

step 2—A mixture of 48 (737 mg, 2.59 mmol), benzyl bromide (0.625 mL, 5.26 mmol) and K2CO3 (734 mg, 5.31 mmol) in DMF (10 mL) was stirred overnight at RT then partitioned between EtOAc and water. The organic layer was thrice washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (0 to 10% EtOAc) to afford 812 mg (84%) of 2-benzyloxy-5-tert-butyl-3-(2-methoxy-pyridin-3-yl)-benzaldehyde (50) as a pale yellow oil.

Workup

  1. customthen partitioned between EtOAc and water
  2. washThe organic layer was thrice washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified by SiO2 chromatography
  7. washeluting with an EtOAc/hexane gradient (0 to 10% EtOAc)

Sources & evidence

ORD record
ord-30b958011c02469f95c12295a7f4365a
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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