Allyl bromide → HCID 66692984, compound

HRID 1469182Notes

Reaction equation

HRID 1469182 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH3:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1.[CH2:16](Br)[CH:17]=[CH2:18].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH2:18]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:4]2[CH:3]=[C:2]([Br:1])[S:6][C:5]=2[CH3:7])=[CH:10][CH:11]=1)[CH:17]=[CH2:16]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 66693659HCID 66693659, compound

Product 1

HCID 66692984HCID 66692984, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of phenol 12 (860 mg, 3.04 mmol) in acetone (20 mL) were added allyl bromide (0.5 mL, 4.56 mmol) and Cs2CO3 (2.0 g, 6.08 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. The reaction mixture was cooled to room temperature and filtered off through celite. The filtrate was concentrated in vacuo. The residue was purified by silica column chromatography (Biotage) to provide the title compound 13 (906 mg, 92%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered off through celite
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica column chromatography (Biotage)

Sources & evidence

ORD record
ord-f227807db5ac47d8983c2b7bba173d76
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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