Allyl bromide → HCID 21873209, compound

HRID 2112314Notes

Reaction equation

HRID 2112314 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH3:9])[CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:16](Br)[CH:17]=[CH2:18]>C1COCC1.[NH4+].[Cl-]>[CH2:18]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=1[CH3:9])[CH:17]=[CH2:16]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 10796Cesium carbonateHCID 168964-Bromo-2-methylphenol

Product 1

HCID 21873209HCID 21873209, compoundYield 45.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A solution of 4-Bromo-2-methyl-phenol (2.0 g, 10.7 mmol) in THF (100 mL) was added solid Cs2CO3 (3.8 g, 11.7 mmol) and allyl bromide (1.9 mL, 21.4 mmol). The reaction mixture was stirred at room temperature for 20 hours. Upon completion, the solution was diluted with aqueous NH4Cl and extracted twice with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), concentrated in vacuo and purified by column chromatography (0 to 100% ethyl acetate in hexanes) to provide 1.1 g (45%) of a white solid.

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography (0 to 100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7823b15e74ef4f7991b7865076de748c
Source dataset
uspto-grants-2009_04
Patent number
US07521439B2

Reaction notes

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