N-bromobutanimide → 1-(3-Bromoprop-1-en-2-yl)-4-chlorobenzene

HRID 2259615Notes

Reaction equation

HRID 2259615 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH3:8])=[CH2:7])=[CH:4][CH:3]=1.[Br:11]N1C(=O)CCC1=O>O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1COCC1>[Br:11][CH2:7][C:6]([C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=1)=[CH2:8]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 743814-Chloro-alpha-methylstyrene

Product 1

HCID 112532501-(3-Bromoprop-1-en-2-yl)-4-chlorobenzeneYield 103.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 31.0 g (0.20 mol) of 4-chloro-α-methylstyrene, 38.0 g (0.21 mol) of N-bromosuccinimide, 3.9 g (0.02 mol) of p-toluenesulfonic acid monohydrate and 610 mL of THF was heated at reflux for 3 h and then concentrated at room temperature. The residue was partitioned between 400 mL of hexanes and 200 mL of H2O, the organic phase was washed twice with 100 mL H2O and dried (MgSO4). Removal of solvent gave 47.8 g of a yellow oil that was used without further purification. 1H NMR (CDCl3, 200 MHz) δ4.33 (s, 2H), 5.50 (d, 2H), 7.2-7.5 (m, 5H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. concentrationconcentrated at room temperature
  4. customThe residue was partitioned between 400 mL of hexanes and 200 mL of H2O
  5. washthe organic phase was washed twice with 100 mL H2O
  6. dry with materialdried (MgSO4)
  7. customRemoval of solvent

Sources & evidence

ORD record
ord-e14518b050724ac1af3f87431bd2e9a9
Source dataset
uspto-grants-1995_12
Patent number
US05474998

Reaction notes

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