Dichloromethane → HCID 67465880, compound

HRID 927318Notes

Reaction equation

HRID 927318 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-].[Na+].ClCCl>BrCCCBr.O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:6][CH2:7][CH2:8][Br:15])([CH2:4][CH2:3][CH2:2][Br:1])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 67465880HCID 67465880, compoundYield 30%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 80011,3-DibromopropaneSolvent

Procedure

The following products are added, in an inert atmosphere, to a solution of 2,7-dibromofluorene (10.0 g, 31.06 mmoles) in 40 ml of 1,3-dibromopropane: first sodium hydroxide (30.0 g, 750.0 mmoles) dissolved in 60 ml of water and finally 0.2 g of tetrabutylammonium bromide. The temperature is brought to 100° C. After 6 hours, after the addition of water, extraction is effected with dichloromethane. After washing the organic phase with water until neutrality, said organic phase is anhydrified on sodium sulfate. The dichloromethane and 1,3-dibromopropane in excess are removed by distillation at reduced pressure. After purification by elution on a chromatographic silica gel column (eluent: heptane/ethyl acetate=99/1), 5.2 g of 2,7-dibromo-9,9-bis(3′-bromopropyl)fluorene are obtained (yield=30%).

Workup

  1. customis brought to 100° C
  2. washAfter washing the organic phase with water until neutrality
  3. customThe dichloromethane and 1,3-dibromopropane in excess are removed by distillation at reduced pressure
  4. customAfter purification
  5. washby elution on a chromatographic silica gel column (eluent: heptane/ethyl acetate=99/1), 5.2 g of 2,7-dibromo-9,9-bis(3′-bromopropyl)fluorene
  6. customare obtained (yield=30%)

Sources & evidence

ORD record
ord-d8e2335a87b64957acdc59b73efadfce
Source dataset
uspto-grants-2016_03
Patent number
US09290483B2

Reaction notes

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