Dimethylformamide → 1-Bromo-5-(but-3-enyloxy)-2,4-dimethylbenzene

HRID 2047947Notes

Reaction equation

HRID 2047947 reaction equation
[Br:1][C:2]1[C:3]([CH3:10])=[CH:4][C:5]([CH3:9])=[C:6]([OH:8])[CH:7]=1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].Br[CH:23]=[CH:24][CH2:25][CH3:26]>O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH2:26][CH2:25][CH:24]=[CH2:23])[C:5]([CH3:9])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 359451-Bromobut-1-eneHCID 126177325-Bromo-2,4-dimethylphenol

Product 1

HCID 594796111-Bromo-5-(but-3-enyloxy)-2,4-dimethylbenzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A 250-mL round bottomed flask is charged with 5-bromo-2,4-dimethylphenol (3.135 g, 15.6 mmol) and dimethylformamide (DMF) (50 mL). Potassium carbonate (23.7 g, 172 mmol) and bromobutene (15.8 mL, 156 mmol) are added and the reaction mixture is heated to 95° C. for 2 hr. After cooling to room temp, water (200 mL) is added. The product is extracted into ether (2×100 mL), and the combined organic fractions are washed with brine, dried over sodium sulfate and dried in vacuo. Yield=3.63 g (91.3%) of light yellow liquid.

Workup

  1. temperatureAfter cooling to room temp
  2. extractionThe product is extracted into ether (2×100 mL)
  3. washthe combined organic fractions are washed with brine
  4. dry with materialdried over sodium sulfate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-eba2d7c18d024c388c7a982b46f758d0
Source dataset
uspto-grants-2013_11
Patent number
US08592615B2

Reaction notes

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