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

HRID 1156183Notes

Reaction equation

HRID 1156183 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-7191bd4b763848cdb81ab6db87781075
Source dataset
uspto-grants-1982_06
Patent number
US04334088

Reaction notes

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