Propargyl bromide → HCID 59678709, compound

HRID 1516074Notes

Reaction equation

HRID 1516074 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH2:12](Br)[C:13]#[CH:14].[C:16](=O)([O-])[O-].[K+].[K+].[NH4+].[Cl-]>CN(C=O)C.C(OCC)C>[CH2:12]([O:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[C:13]#[C:14][CH3:16]

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 162513,4-DimethoxyphenolHCID 25517Ammonium Chloride

Product 1

HCID 59678709HCID 59678709, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To 3,4-dimethoxy phenol (15.4 g, 0.1 mol) in DMF (100 mL) is added propargyl bromide (14.15 g, 0.12 mol) and potassium carbonate (11.88 g, 0.12 mol). The reaction is stirred at room temperature for 12 h, sat. NH4Cl and diethyl ether are added. The organic layers are washed with water, brine and dried over Na2SO4. The crude material is filtered trough a pad of silica (1:1 hexanes:dichloromethane) to afford 4-but-2-ynyloxy-1,2-dimethoxybenzene as a yellow oil.

Workup

  1. washThe organic layers are washed with water, brine
  2. dry with materialdried over Na2SO4
  3. filtrationThe crude material is filtered trough a pad of silica (1:1 hexanes:dichloromethane)

Sources & evidence

ORD record
ord-86f9608c79fe4f17aabfda201484247d
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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