Tetrahydrofuran → HCID 59456279, compound

HRID 1873420Notes

Reaction equation

HRID 1873420 reaction equation
Br[C:2]1[Se:3][CH:4]=[CH:5][CH:6]=1.O.NN.B([O-])=O.[Na+].[F:14][C:15]1[CH:16]=[C:17]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH3:32])=[CH:26][CH:25]=2)[CH:18]=[CH:19][C:20]=1B(O)O.[CH2:33]1[CH2:37]OC[CH2:34]1>CCCCCCC.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:14][C:15]1[CH:16]=[C:17]([C:24]2[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][CH3:32])=[CH:26][CH:25]=2)[CH:18]=[CH:19][C:20]=1[C:2]1[Se:3][C:4]([CH2:34][CH2:33][CH3:37])=[CH:5][CH:6]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 1370132-BromoselenopheneHCID 145326Sodium metaborateHCID 53402576(3-Fluoro-4'-propyl[1,1'-biphenyl]-4-yl)boronic acid

Product 1

HCID 59456279HCID 59456279, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8900HeptaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.0 g (7.33 mmol) of 2-bromoselenophene (purity 92%), 51 mg (0.07 mmol) of bis(triphenylphosphine)palladium(II) chloride, 10 μl (0.2 mmol) of hydrazine hydrate (80%) and 5 ml (5.0 mmol) of aqueous sodium metaborate soln. (1 M) is heated to 60° C. A soln. of 2.11 g (8.1 mmol) of 3-fluoro-4′-propylbiphenyl-4-ylboronic acid in 6 ml of THF is slowly metered in, and the batch is stirred at this temperature for 3 h. After cooling, the mixture is diluted with n-heptane, and the organic phase is separated off. The aqueous phase is extracted with n-heptane, and the combined organic phases are dried using sodium sulfate. The solution is concentrated, and the precipitate forming is filtered off. The residue is purified by column chromatography (SiO2, n-heptane). The further purification is carried out by recrystallisation from n-heptane and from ethanol.

Workup

  1. temperatureAfter cooling
  2. customthe organic phase is separated off
  3. extractionThe aqueous phase is extracted with n-heptane
  4. customthe combined organic phases are dried
  5. concentrationThe solution is concentrated
  6. customthe precipitate forming
  7. filtrationis filtered off
  8. customThe residue is purified by column chromatography (SiO2, n-heptane)
  9. customThe further purification
  10. customis carried out by recrystallisation from n-heptane and from ethanol

Sources & evidence

ORD record
ord-b112e63a89a44e21b805e61383800225
Source dataset
uspto-grants-2012_11
Patent number
US08304036B2

Reaction notes

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