Sodium Iodide → 1,5-Dibromo-3-isopropyl-2-(2-methyl-allyloxy)-benzene

HRID 2290115Notes

Reaction equation

HRID 2290115 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH:9]([CH3:11])[CH3:10])[C:3]=1[OH:12].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Cl[CH2:22][C:23]([CH3:25])=[CH2:24]>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([CH:9]([CH3:10])[CH3:11])[C:3]=1[O:12][CH2:24][C:23]([CH3:25])=[CH2:22]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium CarbonateHCID 154540732,4-Dibromo-6-isopropylphenol2×

Product 1

HCID 154540751,5-Dibromo-3-isopropyl-2-(2-methyl-allyloxy)-benzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Following general procedure B and using 2,4-dibromo-6-isopropyl-phenol (Compound 4, 76.56 g, 0.25 mol), potassium carbonate (41.46 g, 0.3 mol), sodium iodide (3.75 g, 0.025 mol) and 3-chloro-2-methylpropene (74 mL, 0.375 mol) in 1L of acetone, the title compound was obtained as a yellow oil. 1H NMR (300 MHz, CDCl3): δ 7.52 (d, 1H, J=2.2 Hz), 7.30 (d, 1H, J=2.2 Hz), 5.17 (s, 1H), 5.01 (s, 1H), 4.29 (s, 2H), 3.29 (heptet, 1H, J=6.9 Hz), 1.91 (s, 3H), 1.23 (d, 6H, J=6.7 Hz).

Sources & evidence

ORD record
ord-30e7af5fefd64f24ae48e76cf98aac36
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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