Dichloromethane → Methyl 1-(bromomethyl)cyclopropane-1-carboxylate

HRID 2104371Notes

Reaction equation

HRID 2104371 reaction equation
C1(P([C:14]2[CH:19]=[CH:18]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Br:24])(Br)(Br)Br.[C:25](=[O:28])([O-])[OH:26].[Na+].[CH2:30](Cl)Cl>>[CH3:30][O:26][C:25]([C:18]1([CH2:20][Br:24])[CH2:19][CH2:14]1)=[O:28]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium Bicarbonate

Product 1

HCID 19767911Methyl 1-(bromomethyl)cyclopropane-1-carboxylate

Procedure

To a solution of the compound obtained in Referential Example 162 (4.20 g) in methylene chloride (168 mL) were added triphenylphosphine (10 g) and carbon tetrabromide (16 g) at room temperature under nitrogen atmosphere, and after 2 minutes, saturated aqueous sodium hydrogencarbonate was added thereto. The organic layer was washed with saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate hexane=1:19), to thereby give the title compound (2.15 g).

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialwas dried over sodium sulfate anhydrate
  3. distillationThe solvent was distilled away under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate hexane=1:19)

Sources & evidence

ORD record
ord-a082e70062a3430486e2231ad714c63a
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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