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

HRID 1390135Notes

Reaction equation

HRID 1390135 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 5360545SodiumHCID 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-7612a83d9fc641fc92e8f8b2e54307c0
Source dataset
uspto-grants-1981_01
Patent number
US04247715

Reaction notes

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