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

HRID 902855Notes

Reaction equation

HRID 902855 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-e10f3ff3e71d4ff49378cfb72769ff70
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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