Benzyl Bromide → HCID 66688579, compound

HRID 337097Notes

Reaction equation

HRID 337097 reaction equation
[CH2:1]([C:3]([CH2:14][CH3:15])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13])[C:4]([NH2:6])=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.O>[CH2:14]([C:3]([CH2:1][CH3:2])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:4]([NH2:6])=[O:5])[CH3:15]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 86663250HCID 86663250, compound

Product 1

HCID 66688579HCID 66688579, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of α,α-diethyl-2-hydroxy-benzeneacetamide (Example 266b, 1.21 g) in DMF (9.93 mL) was treated with potassium carbonate (0.807 g) and benzyl bromide (0.694 mL) under nitrogen. The resulting mixture was stirred at room temperature for 16 h. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated. The crude product was purified (SiO2 chromatography eluting with 30-100% ethyl acetate in iso-hexane) to afford the subtitle product (0.77 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product was purified
  6. wash(SiO2 chromatography eluting with 30-100% ethyl acetate in iso-hexane)

Sources & evidence

ORD record
ord-897e1deaf65a4e29be00faa997bc4174
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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