1-Indanone → 6-Chloro-inden-1-one

HRID 2036185Notes

Reaction equation

HRID 2036185 reaction equation
C1(=O)C2C(=CC=CC=2)CC1.Br[CH:12]1[C:20]2[C:15](=[CH:16][C:17]([Cl:21])=[CH:18][CH:19]=2)[C:14](=[O:22])[CH2:13]1.C(N(CC)CC)C>O1CCCC1>[Cl:21][C:17]1[CH:16]=[C:15]2[C:20]([CH:12]=[CH:13][C:14]2=[O:22])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 67351-IndanoneHCID 8471TriethylamineHCID 20463006HCID 20463006, compound

Product 1

HCID 866749156-Chloro-inden-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Further exemplary methods of synthesis include conversion of indanone A to intermediate C via treatment of 3-bromo-6-chloro-indan-1-one (A; for references on this material, see: Bøgesø EP 35363 A1 19810909 and Kehler, Juhl, Püschl, WO 2008025361; each herein incorporated by reference in its entirety) with a base such as triethylamine in a solvent such as tetrahydrofuran at ambient temperature (Scheme 1). Removal of the precipitated amine hydrobromide salt by filtration and concentration of the filtrate will afford 6-chloro-inden-1-one (B). This material can be reacted with phenyl-d5-boronic acid in the presence of approximately 1 equivalent of a base such as triethylamine and a catalytic amount of a 1:1 mixture of [Rh(ndb)2]BF4 (bis(norbornadiene)rhodium(I) tetrafluoroborate) and racemic BINAP (2,2′-bis(diphenylphosphino)-1,1′-binaphthyl) in a suitable solvent (e.g. approximately 10:1 solvent mixture of 1,4-dioxane and water) under an atmosphere of argon at elevated temperature (e.g. about 100° C.). Work-up will afford racemic 6-chloro-3-phenyl-d5-indan-1-one (C).

Workup

  1. customFurther exemplary methods of synthesis
  2. customat ambient temperature
  3. customRemoval of the precipitated amine hydrobromide salt
  4. filtrationby filtration and concentration of the filtrate

Sources & evidence

ORD record
ord-37f1c8d681b44aecb3462c75bfeaed6f
Source dataset
uspto-grants-2013_11
Patent number
US08575174B2

Reaction notes

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