Diisopropylethylamine → 1-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene

HRID 18180

Reaction equation

HRID 18180 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([I:9])[C:3]=1[OH:10].[CH2:11](Br)[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([I:9])[C:3]=1[O:10][CH2:11][CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98116BromomethylstyreneHCID 593449072-Bromo-6-iodo-4-methylphenol

Product 1

HCID 685856031-Bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzeneYield 101.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-4-methyl-6-iodophenol (7.82 gm, 25 mmol) and cinnamyl bromide (4.93 g, 25 mmol) were added to DMF (20 ml). Diisopropylethylamine (5.3 ml, 30.4 mmol) was added and the mixture heated to 60° C. for 15 minutes and then allowed stir for 16 hours at room temperature. The DMF was removed under vacuum, and 1M HCl was added until the residue was acidic. The mixture was extracted with ethyl acetate, and the combined organic phase was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 1-bromo-3-iodo-5-methyl-2-(3-phenylallyloxy)-benzene (10.86 g, 100% yield).

Workup

  1. customThe DMF was removed under vacuum, and 1M HCl
  2. additionwas added until the residue
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe combined organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c9bb23be4d014b61b2df65620189bc16
Source dataset
uspto-grants-2010_06
Patent number
US07741326B2

Linked notes

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