N-bromobutanimide → Methyl trans-2-methoxy-5-bromomethylcinnamate

HRID 615506Notes

Reaction equation

HRID 615506 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][C:4]=1/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8].[Br:16]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:12]([CH2:15][Br:16])=[CH:11][C:4]=1/[CH:5]=[CH:6]/[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 70480073Methyl cis-2-methoxy-5-methylcinnamate

Product 1

HCID 20428665Methyl trans-2-methoxy-5-bromomethylcinnamate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

As described in step b. of Example 16 methyl cis-2-methoxy-5-methylcinnamate was treated with N-bromosuccinimide in carbon tetrachloride to provide the oily title compound which was purified by chromatography on silica gel with ether/hexane: NMR in CDCl3 (δ units) 3.76 and 3.83 (singlet, 3); 4.43 (singlet, 2); 6.47 and 7.92 (doublet, J=16 Hz, 1); 6.83 (doublet, J=9 Hz, 1); 7.65 (multiplet, 2).

Sources & evidence

ORD record
ord-831bf33dbe99444b8903b237938ca54d
Source dataset
uspto-grants-1985_02
Patent number
US04499299

Reaction notes

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