Ethyl 3-(4-bromophenyl)-3-oxopropanoate → HCID 178472889, compound

HRID 1865108Notes

Reaction equation

HRID 1865108 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[N:16]([O-])=[O:17].[Na+]>C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](=[O:15])[C:9](=[N:16][OH:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2757149Ethyl 3-(4-bromophenyl)-3-oxopropanoateHCID 23668193Sodium Nitrite

Product 1

HCID 178472889HCID 178472889, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
1 °C

Procedure

Crude ethyl 3-(4-bromophenyl)-3-oxopropanoate (24.5 g, 0.0884 mol) is dissolved in acetic acid (250 mL) at 23° C. under nitrogen, and water (60 mL) is added. The mixture is cooled to 1° C., and a solution of sodium nitrite (7.63 g, 0.111 mol) in water (60 mL) is added dropwise while maintaining the reaction temperature between 1 to 3° C. The mixture is allowed to stir at 1° C. for 3 hours. Water (100 mL) is added dropwise to the cooled reaction mixture to precipitate the product. The cold (about 5° C.) mixture is suction filtered and the collected solids are rinsed with cold 1:1 (v/v) HOAc/water (50 mL), followed by water (2×50 mL). The solids are suction dried overnight to give 18.3 g of crude title compound.

Workup

  1. temperaturewhile maintaining the reaction temperature between 1 to 3° C
  2. customto precipitate the product
  3. customThe cold (about 5° C.) mixture
  4. filtrationfiltered
  5. washthe collected solids are rinsed with cold 1:1 (v/v) HOAc/water (50 mL)
  6. customThe solids are suction dried overnight

Sources & evidence

ORD record
ord-553229798e1046c7bc5fe0c2dc6175f9
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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