Sodium Iodide → 2,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether

HRID 2290114Notes

Reaction equation

HRID 2290114 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[OH:10].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:20][C:21]([CH3:23])=[CH2:22]>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[O:10][CH2:22][C:21]([CH3:23])=[CH2:20]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 118612,4-Dibromo-6-methylphenol

Product 1

HCID 154540742,4-Dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2,4-dibromo-6-methyl-phenol (Compound 3,62 g, 0.23 mol) in 700 mL of acetone was treated with potassium carbonate (38.7 g, 0.28 mol), sodium iodide (3.4 g, 0.023 mol) and 3-chloro-2-methylpropene (34 mL, 0.35 mol) and the resulting suspension was refluxed for 18 hours. The solids were filtered and the filtrate was evaporated in vacuo to afford the title compound as a dark yellow oil. 1H-NMR (300 MHz, CDCl3): δ 7.53(d, 1H, J=2.7 Hz), 7.27(d, 1H, J=1.9 Hz), 5.17(s, 1H), 5.02(s, 1H), 4.28(s, 2H), 2.30(s, 3H), 1.92(s, 3H).

Workup

  1. temperaturethe resulting suspension was refluxed for 18 hours
  2. filtrationThe solids were filtered
  3. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-f82c4cb0677f41e2958cc98630730ecb
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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