Benzene, 1-(chloromethyl)-3(or 4)-ethenyl- → HCID 131730513, compound

HRID 1967082Notes

Reaction equation

HRID 1967082 reaction equation
[C:1]12([CH2:8][Mg]Br)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2.[CH:11]([CH:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH2:12]>C1COCC1>[C:1]12([CH2:8][CH2:12][CH:11]=[CH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[CH:2]2

Participants

4

Reactant 2

HCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-HCID 178419656HCID 178419656, compound

Product 1

HCID 131730513HCID 131730513, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Monomer norbornenylethylstyrene (N) was first synthesized as shown in FIG. 1. Norbornenylmethyl bromide (mainly the endo isomer) was treated with magnesium in THF to form the corresponding Grignard reagent. In the presence of a catalytic amount of Li2CuCl4, this norbornenylmethyl magnesium bromide (1.15 equiv) was coupled with vinylbenzyl chloride (1 equiv) at −78° C. in THF to produce the p-norbornenylethylstyrene (N) in a conversion of 85%. The 13C and 1H NMR spectra of purified N (silica column/hexanes) indicated a product of high purity and all resonances were consistent with the structure.

Sources & evidence

ORD record
ord-6a0aa0dc53c74d8cb78d21dd7922f5b1
Source dataset
uspto-grants-2013_04
Patent number
US08420704B2

Reaction notes

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