N,N-Dimethylbenzylamine → HCID 54129135, compound

HRID 2073646Notes

Reaction equation

HRID 2073646 reaction equation
Cl[C:2]([C:4]1[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=1)=O.[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=C)=[CH:20][CH:19]=1.C(N(C)C)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC(C)=CC=1>[Br:17][C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:2][C:4]2[CH:16]=[CH:15][C:7]([CH:8]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:5]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7681N,N-DimethylbenzylamineHCID 162634-BromostyreneHCID 54300281HCID 54300281, compound

Product 1

HCID 54129135HCID 54129135, compoundYield 10.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Conditions

Temperature
130 °C

Procedure

4.77 g (20 mmols) of ethyl 4-chloroformylcinnamate, 4.04 g (20 mmols) of 4-bromostyrene, 2.72 g (20 mmols) of N-benzyldimethylamine and 0.0448 g (0.2 mmol) of palladium acetate are added under argon to 50 ml of p-xylene, and the reaction mixture is stirred at 130° C. for 1.5 hours. The product which has been precipitated is filtered off at room temperature and is then recrystallised from methanol. 0.73 g (10% of theory) of ethyl 4-bromostilbene-4'-acrylate is obtained in the form of yellow crystals; melting point 166.9° C.

Workup

  1. customThe product which has been precipitated
  2. filtrationis filtered off at room temperature
  3. customis then recrystallised from methanol

Sources & evidence

ORD record
ord-262f14ce4c324c6e97b63cf284583402
Source dataset
uspto-grants-1990_04
Patent number
US04918215

Reaction notes

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