Ethyl bromoacetate → Ethyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate

HRID 1578171Notes

Reaction equation

HRID 1578171 reaction equation
[Na].[Cl:2][C:3]1[C:11]([Cl:12])=[C:10]2[C:6]([CH2:7][CH:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:9]2=[O:13])=[CH:5][C:4]=1[OH:20].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[Cl:2][C:3]1[C:11]([Cl:12])=[C:10]2[C:6]([CH2:7][CH:8]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:9]2=[O:13])=[CH:5][C:4]=1[O:20][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 5360545Sodium2×HCID 127740892-Phenyl-5-hydroxy-6,7-dichloro-1-indanone

Product 1

HCID 12774090Ethyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetateYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium (629 mg., 27.3 mmol) is added to 50 ml. of absolute ethanol under a nitrogen atmosphere. After the sodium dissolves, 6,7-dichloro-5-hydroxy-2-phenyl-1-indanone (7.35 g., 25.1 mmol), and 75 ml. of additional absolute ethanol are added followed by 3.1 ml. of ethyl bromoacetate (28.1 mmol). The mixture is stirred at room temperature for 1 to 2 hrs., refluxed for 5-16 hrs. and then poured into a dilute acid-ether mixture. The crude reaction product collected and crystallized from 1:1 ethanol-water with activated charcoal provides a 70% yield of ethyl (6,7-dichloro-1-oxo-2-phenyl-5-indanyloxy)acetate, m.p. 113.5°-115°.

Workup

  1. temperature, refluxed for 5-16 hrs
  2. customThe crude reaction product
  3. customcollected
  4. customcrystallized from 1:1 ethanol-water with activated charcoal

Sources & evidence

ORD record
ord-2d09014ced0749adbc282f6b61d9398c
Source dataset
uspto-grants-1981_09
Patent number
US04291168

Reaction notes

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