Methyl Methacrylate → Methyl Methacrylate 1-Phenylethyl Bromide CuCl

HRID 1264140Notes

Reaction equation

HRID 1264140 reaction equation
[Cl:1][Cu:2].CCCCC(C1C=CN=C(C2C=C(C(CCCC)CCCC)C=CN=2)C=1)CCCC.C1(OC2C=CC=CC=2)C=CC=CC=1.[C:46]([O:51][CH3:52])(=[O:50])[C:47]([CH3:49])=[CH2:48].[C:53]1([CH:59]([Br:61])[CH3:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>>[C:46]([O:51][CH3:52])(=[O:50])[C:47]([CH3:49])=[CH2:48].[C:53]1([CH:59]([Br:61])[CH3:60])[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1.[Cl:1][Cu:2]

Participants

6

Reactant 5

HCID 6658Methyl MethacrylateHCID 7583Diphenyl EtherHCID 11454(1-Bromoethyl)benzeneHCID 62652Cuprous chlorideHCID 1749844,4'-Bis(1-butylpentyl)-2,2'-bipyridine

Product 1

HCID 86758899Methyl Methacrylate 1-Phenylethyl Bromide CuCl

Procedure

A dry round-bottomed flask was charged with CuCl (23.2 mg; 0.234 mmol), 4,4′-di(5-nonyl)-2,2′-bipyridine (190.9 mg; 0.468 mmol) and diphenyl ether (10.0 ml). The flask was sealed with a rubber septum and was cycled between vacuum and argon three times to remove the oxygen. Degassed methyl methacrylate (10.0 ml; 93.6 mmol) was added using degassed syringes and stainless steel needles. The 1-phenylethyl bromide (64 mL; 0.468 mmol) was added and the flask was immersed in an oil bath held by a thermostat at 90° C. At various times samples were taken via syringe to monitor conversion (GC) and molecular weight (SEC).

Workup

  1. customThe flask was sealed with a rubber septum
  2. customto remove the oxygen
  3. customusing degassed syringes and stainless steel needles
  4. customthe flask was immersed in an oil bath
  5. customheld by a thermostat at 90° C
  6. customAt various times samples were taken via syringe

Sources & evidence

ORD record
ord-42a3b215bdbf40a6928b869931bd7168
Source dataset
uspto-grants-2003_04
Patent number
US06541580B1

Reaction notes

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