Bromine → HCID 18790631, compound

HRID 1107029Notes

Reaction equation

HRID 1107029 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:12])#[N:2].[Br:13]Br>C(Cl)(Cl)Cl>[Br:13][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[CH:11][C:3]=2[C:1]#[N:2])[C:7]1=[O:12]

Participants

4

Reactant 2

HCID 24408BromineHCID 27515831-Oxo-2,3-Dihydro-1H-Indene-4-Carbonitrile

Product 1

HCID 18790631HCID 18790631, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

2-Bromo-4-cyano-1-indanone can be obtained in the following way: a solution of 6.9 g of 4-cyano-1-indanone and 95 ml of chloroform is cooled to 5° C. A solution of 7.04 g of bromine and 20 ml of chloroform is then added dropwise over two hours at a temperature of between 0 and 5° C. After having left the reaction mixture stirring for one hour, the temperature of introduction being retained, the solution is allowed to return to room temperature and stirring is continued overnight. The reaction mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C. The residue thus obtained is purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar), with an ethyl ether/cyclohexane (20/80 by volume) mixture as eluent. 3.43 g of 2-bromo-4-cyano-1-indanone are thus obtained, which product melts at 124° C.

Workup

  1. waitAfter having left the reaction mixture
  2. customto return to room temperature
  3. stirringstirring
  4. waitis continued overnight
  5. concentrationThe reaction mixture is then concentrated to dryness under reduced pressure (15 mm Hg; 2 kPa) at 40° C
  6. customThe residue thus obtained
  7. customis purified by flash chromatography on a silica column, under a nitrogen stream at medium pressure (0.5 bar)

Sources & evidence

ORD record
ord-5c0f9fbc23534183a9d010e84c736c85
Source dataset
uspto-grants-2000_05
Patent number
US06057454

Reaction notes

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