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Hexane → 2-[p-(2,2-Dibromovinyl)phenyl]-5-pentylpyrimidine

HRID 370681
Notes
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Reaction equation

HRID 370681 reaction equation
[Br:1][C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([C:30]1[CH:31]=[N:32][C:33]([C:36]2[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][CH:37]=2)=[N:34][CH:35]=1)[CH2:26][CH2:27][CH2:28][CH3:29].CCCCCC>C(Cl)Cl>[Br:1][C:2]([Br:5])=[CH:40][C:39]1[CH:38]=[CH:37][C:36]([C:33]2[N:32]=[CH:31][C:30]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:35][N:34]=2)=[CH:43][CH:42]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 20274898p-(5-Pentyl-2-pyrimidinyl)benzaldehyde

Product 1

HCID 202750122-[p-(2,2-Dibromovinyl)phenyl]-5-pentylpyrimidineYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Conditions

Temperature
0 °C

Procedure

A solution of 5.44 g of tetrabromomethane in 80 ml of methylene chloride was placed at 0° C. under argon gasification in a sulphonation flask equipped with a mechanical stirrer and treated within 10 minutes with a solution of 8.6 g of triphenylphosphine in 20 ml of methylene chloride. After completion of the addition, the clear orange solution was stirred at 0° C. for a further 5 minutes and then a solution of 2.08 g of p-(5-pentyl-2-pyrimidinyl)benzaldehyde in 15 ml of methylene chloride was added dropwise within 5 minutes. The mixture was subsequently stirred at 0° C. for a further 30 minutes, then the flask content was poured into 700 ml of hexane and the precipitate which thereby separated was filtered off (rinsing with hexane). The concentrated filtrate was digested with 200 ml of hexane, left to stand at 0° C. for 18 hours, filtered (rinsing with hexane) and the filtrate was concentrated. Low-pressure chromatography (0.5 bar) of the residue (3.7 g) on silica gel with 3% ethyl acetate/petroleum ether gave 2.70 g (80%) of 2-[p-(2,2-dibromovinyl)phenyl]-5-pentylpyrimidine as colourless crystals (purity 94.5%); m.p. 74° C.

Workup

  1. customwas placed at 0° C. under argon
  2. customequipped with a mechanical stirrer
  3. additionAfter completion of the addition
  4. stirringThe mixture was subsequently stirred at 0° C. for a further 30 minutes
  5. customthe precipitate which thereby separated
  6. filtrationwas filtered off
  7. wash(rinsing with hexane)
  8. waitleft
  9. waitto stand at 0° C. for 18 hours
  10. filtrationfiltered
  11. wash(rinsing with hexane)
  12. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-277277b7dfbe4a59aa534f7867466867
Source dataset
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04528114

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes