Water → Methyl 2-(2-bromophenyl)-5-chloropentanoate

HRID 2235795Notes

Reaction equation

HRID 2235795 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH3:12])=[O:10].[H-].[Na+].[Cl:15][CH2:16][CH2:17][CH2:18]I.O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([CH2:18][CH2:17][CH2:16][Cl:15])[C:9]([O:11][CH3:12])=[O:10]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropaneHCID 8063364Methyl 2-(2-bromophenyl)acetate

Product 1

HCID 67067456Methyl 2-(2-bromophenyl)-5-chloropentanoate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 2-bromophenylacetate (2.0 g) in DMF (5 mL) was added to a suspension of sodium hydride (containing mineral oil at 40%, 384 mg) in DMF (20 mL) under ice-cooling. The reaction solution was stirred for 10 minutes, further stirred at room temperature for 30 minutes and then ice-cooled again. A solution of 1-chloro-3-iodopropane (1.96 g) in DMF (5 mL) was added to the reaction mixture, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of methyl 2-(2-bromophenyl)-5-chloropentanoate. Hydrazine monohydrate (4 mL) was added to a solution of the resulting crude methyl 2-(2-bromophenyl)-5-chloropentanoate (2.895 g) in ethanol (20 mL), and the reaction solution was stirred at room temperature for three hours. Hydrazine monohydrate (8 mL) was further added to the reaction solution, and the reaction solution was stirred at room temperature for two days. The reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate and were added to the residue, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain 1.504 g of the crude purified title compound. The property value of the compound is as follows.

Workup

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 30 minutes
  3. temperatureice-cooled again
  4. stirringthe reaction solution was stirred at room temperature overnight
  5. customthe organic layer was separated
  6. washThe resulting organic layer washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e644c008bd1347abacf66f1195dc2ee3
Source dataset
uspto-grants-2010_05
Patent number
US07713993B2

Reaction notes

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