2-Bromopropene → 1,3-Dibromo-5-(prop-1-en-2-yl)benzene

HRID 2071043Notes

Reaction equation

HRID 2071043 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[C:6]([Br:8])[CH:7]=1.Br[C:13]([CH3:15])=[CH2:14]>C1COCC1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:13]([CH3:15])=[CH2:14])[CH:5]=[C:6]([Br:8])[CH:7]=1

Participants

6

Reactant 2

HCID 112022-BromopropeneHCID 27346893,5-Dibromobenzeneboronic acid

Product 1

HCID 214681951,3-Dibromo-5-(prop-1-en-2-yl)benzene

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
40 °C

Procedure

To a degassed mixture of 5.0 g (17.9 mmol) of 3,5-dibromophenylboronic acid in 50 mL of THF and 25 mL of 2 M Na2CO3 (aqueous) was added 1.13 g (0.975 mmol) of Pd(PPh3)4 and 2.3 mL of 2-bromopropene. The mixture was stirred at 40° C. for 5 h, and the mixture was extracted with EtOAc. The organic layer was washed with 25 mL of brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (10% EtOAc/hexanes) provided 1,3-dibromo-5-(prop-1-en-2-yl)benzene with some impurity.

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic layer was washed with 25 mL of brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash silica gel chromatography (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b781517e53c041fbabd798b2a3d66aaf
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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