Ethyl bromoacetate → HCID 89618015, compound

HRID 1502569Notes

Reaction equation

HRID 1502569 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].Br[CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Li+].C[Si]([N-][Si](C)(C)C)(C)C>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH:5]1[CH2:4][C:3]2[C:7](=[CH:8][CH:9]=[CH:10][C:2]=2[Br:1])[C:6]1=[O:11])[CH3:18]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 987131-Indanone, 4-bromo-

Product 1

HCID 89618015HCID 89618015, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 2733832Lithium HexamethyldisilazideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromoindanone (15.8 g, 75 mmol) at −78° C. was added LiHMDS (1 M in THF, 90 mL). The slight brown solution was allowed to warm up to 0° C., and was cooled again to −75° C. and ethyl 2-bromoacetate (9.1 mL, 82 mmol) was added dropwise. The mixture was allowed to warm up over night (−75° C. to −20° C. over 12 h). The mixture was quenched with sat. ammonium chloride and was extracted with ethyl acetate. Flash chromatography give 19.5 g of the title compound in a mixture with the starting indanone ethyl 2-[4-bromo-2-(2-ethoxy-2-oxo-ethyl)-1-oxo-indan-2-yl]acetate and which was used without further purification for the next step (purity, 60% of the desired product). LC-MS (Method A) RT 1.11 min., 297/299 (M+H+).

Workup

  1. temperaturewas cooled again to −75° C.
  2. temperatureto warm up over night (−75° C. to −20° C. over 12 h)
  3. customThe mixture was quenched with sat. ammonium chloride
  4. extractionwas extracted with ethyl acetate

Sources & evidence

ORD record
ord-3738782371844e68a588b46901e9e14b
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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