Dichloromethane → HCID 86758110, compound

HRID 2184907Notes

Reaction equation

HRID 2184907 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](/[C:9](/[CH3:16])=[CH:10]\[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[Br:17]N1C(=O)CCC1=O.ClCCl>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5](/[C:9](/[CH2:16][Br:17])=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 67184N-bromobutanimideHCID 86758111HCID 86758111, compound

Product 1

HCID 86758110HCID 86758110, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of ethyl (Z) 3-(3-cyanophenyl)-2-butenoate (2 g, 9.3 mmol) in 50 ml carbon tetrachloride was added N-bromosuccinimide (1.74 g, 9.77 mmol) and benzoyl peroxide (40 mg, 0.165 mmol). Reaction mixture was heated to reflux and stirred over night. Reaction was allowed to cool to room temperature to which 50 ml dichloromethane was added. Organic was washed with 2×50 ml water, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude residue was chromatographed on silica gel using 2.5% EtOAc in hexane as the eluent to give ethyl (Z) 3-(3-cyanophenyl)-4-bromo-2-butenoate (0.77 g, 29%) as a clear oil (note: NOE experiment showed compound isomerized during bromination). H1NMR (CDCl3) 1.311-1.347 (t, 3H); 4.239-4.292 (m, 2H); 4.92 (s, 2H); 6.18 (s, H); 7.514-7.801 (m, 4H). ES-MS (M+H+): 293.95 and 296.0

Workup

  1. customReaction mixture
  2. temperaturewas heated
  3. temperatureto reflux
  4. customReaction
  5. additionwas added
  6. washOrganic was washed with 2×50 ml water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customCrude residue was chromatographed on silica gel using 2.5% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-936eb8e0c4954eb49ff50a77d709caf2
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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