1,2-Dibromoethane → Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

HRID 1453040

Reaction equation

HRID 1453040 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1.[H-].[Na+].Br[CH2:16][CH2:17]Br>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=2)[CH2:17][CH2:16]1)=[O:12]

Participants

6

Reactant 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 11746402Methyl 2-(3-bromophenyl)acetate

Product 1

HCID 58762755Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (3-Bromo-phenyl)-acetic acid methyl ester (4.54 g, 20 mmol) dissolved in dry THF (10 mL) was added dropwise to suspension of NaH (95% dry, 1.05 g, 44 mmol) in DMF (40 mL) and THF (10 mL), under a nitrogen atmosphere, at 0° C. After 30 min, gas evolution ceased, and 1,2-dibromoethane (3.79 mL, 44 mmol) was added dropwise over 20 min. The resulting mixture was stirred for 1 h, then quenched with 1N HCl, extracted with ether, washed with brine, dried over MgSO4, and stripped of solvent. The resulting oil was distilled under high vacuum. The product was collected between 95° C. and 105° C. Yield 2 g, 39%.

Workup

  1. customquenched with 1N HCl
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. distillationThe resulting oil was distilled under high vacuum
  6. customThe product was collected between 95° C. and 105° C

Sources & evidence

ORD record
ord-f4910d47ca8545baa42bf4187e7af02e
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Linked notes

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