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

HRID 1392748Notes

Reaction equation

HRID 1392748 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>>[Br:24][CH2:20][C:18]1([C:25]([O:26][CH3:30])=[O:28])[CH2:19][CH2:14]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium Bicarbonate

Product 1

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

Procedure

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

Workup

  1. washAfter the resultant organic layer was washed with saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe resultant residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:19)

Sources & evidence

ORD record
ord-e440a6f2d96645a59fdfd10cb4b7ae62
Source dataset
uspto-grants-2008_03
Patent number
US07342014B2

Reaction notes

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