Carbon tetrabromide → HCID 19759459, compound

HRID 1586817Notes

Reaction equation

HRID 1586817 reaction equation
[Cl:1][C:2]1[N:6]([CH3:7])[CH:5]=[C:4]([C:8]#[N:9])[C:3]=1[C:10]1[CH:15]=[CH:14][C:13]([CH2:16]O)=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:38]>C(Cl)Cl>[Br:38][CH2:16][C:13]1[CH:14]=[CH:15][C:10]([C:3]2[C:4]([C:8]#[N:9])=[CH:5][N:6]([CH3:7])[C:2]=2[Cl:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19759367HCID 19759367, compound

Product 1

HCID 19759459HCID 19759459, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-chloro-4-(4-hydroxymethylphenyl)-1-methylpyrrole-3-carbonitrile (450 mg) in methylene chloride (20 ml) was added triphenylphosphine (1.44 g) and carbon tetrabromide (1.21 g) successively at 0° C. and the resulting yellow solution was stirred at the same temperature for a while. The mixture was washed with aqueous saturated sodium bicarbonate and water, dried over magnesium sulfate and filtered. The organic layer was concentrated in vacuo and the residue was purified by flash chromatography eluted with a mixture of ethyl acetate and n-hexane 1:4 (V/V) then with 1:3 (V/V) to give 4-(4-bromomethylphenyl)-5-chloro-1-methylpyrrole-3-carbonitrile (220 mg) as a white solid.

Workup

  1. washThe mixture was washed with aqueous saturated sodium bicarbonate and water
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe residue was purified by flash chromatography
  6. washeluted with a mixture of ethyl acetate and n-hexane 1:4 (V/V)

Sources & evidence

ORD record
ord-9991cf94ade74c3e82f86431bc0b2439
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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