Bromoform → 39647-01-3

HRID 1385181Notes

Reaction equation

HRID 1385181 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH:8]([Br:11])(Br)[Br:9]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.[OH-].[Na+]>[Br:9][C:8]1([Br:11])[CH2:3][C:2]1([CH3:4])[C:1]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 5558BromoformHCID 6658Methyl Methacrylate

Product 1

HCID 363499339647-01-3Yield 75.6%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of methyl methacrylate (3.15 g, 31.6 mmol), benzyltriethylammonium chloride (TEBA) (0.72 g, 10 mol %), in 12.6 mL of 50% sodium hydroxide solution was added bromoform (15.95 g, 63 mmol). The reaction was stirred overnight and then extracted with dichloromethane (2×25 mL). The organic extracts were washed with brine, dried (MgSO4), and then condensed in vacuo. The residue was purified by bulb to bulb distillation to give 6.5 g of the known product as an oil. 1H NMR (CDCl3) δ3.8 (s, 3H), 2.4(d, 1H), 1.6 (s, 3H), 1.5 (d, 1H).

Workup

  1. extractionextracted with dichloromethane (2×25 mL)
  2. washThe organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customcondensed in vacuo
  5. distillationThe residue was purified by bulb to bulb distillation

Sources & evidence

ORD record
ord-73630f2ea9e84001bfb59a121042e6a9
Source dataset
uspto-grants-2001_07
Patent number
US06262099B1

Reaction notes

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