Benzyl Bromide → HCID 59153173, compound

HRID 2355265Notes

Reaction equation

HRID 2355265 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:15][C:16]1[C:21]([I:22])=[C:20]([OH:23])[CH:19]=[CH:18][C:17]=1[C:24](=[O:29])[CH2:25][CH:26]([CH3:28])[CH3:27]>CN(C)C=O>[CH2:1]([O:15][C:16]1[C:21]([I:22])=[C:20]([O:23][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:19]=[CH:18][C:17]=1[C:24](=[O:29])[CH2:25][CH:26]([CH3:27])[CH3:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 59153170HCID 59153170, compound

Product 1

HCID 59153173HCID 59153173, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add benzyl bromide (17.63 g, 103.1 mmol, 12.3 mL) and cesium carbonate (30.53 g, 93.7 mmol) to a solution of 1-(2,4-dihydroxy-3-iodo-phenyl)-3-methyl-butan-1-one (15.00 g, 46.9 mmol) in anhydrous dimethylformamide (120 mL) at room temperature under Argon gas. Stir the reaction at room temperature overnight. Filter the mixture and concentrate the filtrate under reduced pressure to an oil. Partition the oil between ether and water. Separate the organic layer and extract the aqueous layer with ether (2×). Combine the organic layers, wash with brine, dry over sodium sulfate, filter and concentrate to provide a redish oil (22.5 g, 45 mmol, 96% yield). MS (m/z): 501 (M+1).

Workup

  1. customthe reaction at room temperature overnight
  2. filtrationFilter the mixture
  3. concentrationconcentrate the filtrate under reduced pressure to an oil
  4. customPartition the oil between ether and water
  5. customSeparate the organic layer
  6. extractionextract the aqueous layer with ether (2×)
  7. washCombine the organic layers, wash with brine
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate

Sources & evidence

ORD record
ord-43d97d7b413643db85ce7f6696aa9e66
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…