Benzyl Bromide → HCID 67428317, compound

HRID 2190926Notes

Reaction equation

HRID 2190926 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:12])([CH3:11])[O:8][C:7](=[O:13])[C:6]=2[CH:14]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[CH2:15]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][C:9]([CH3:11])([CH3:12])[O:8][C:7](=[O:13])[C:6]=2[CH:14]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 67421272HCID 67421272, compound

Product 1

HCID 67428317HCID 67428317, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 500 mg 6-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (2.57 mmol), 550 mg benzyl bromide (3.22 mmol), and 922 mg cesium carbonate (2.8 mmol) in 8.6 mL of anhydrous DMF were stirred at room temperature for 18 hours. The mixture was diluted with ethyl acetate and washed successively with water, saturated sodium bicarbonate, and brine solutions. The organic fraction was dried over sodium sulfate and concentrated under reduced pressure to give a crude residue which was further purified by column chromatography, eluting from silica gel with a gradient of 10 to 50% ethyl acetate in hexanes, to give the desired product as a pale yellow solid. MS: (+) m/z 285.10 (M+1)

Workup

  1. washwashed successively with water, saturated sodium bicarbonate, and brine solutions
  2. dry with materialThe organic fraction was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give a crude residue which
  5. customwas further purified by column chromatography
  6. washeluting from silica gel with a gradient of 10 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6da71af45c0142ab9d7d5d78e46d331d
Source dataset
uspto-grants-2012_12
Patent number
US08324405B2

Reaction notes

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