Carbon tetrabromide → HCID 15895428, compound

HRID 1457226Notes

Reaction equation

HRID 1457226 reaction equation
[CH3:1][C:2]1[C:3]([N:8]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])[S:9]([C:12]2[C:13]([C:18]3[CH:23]=[CH:22][C:21]([C:24]4[O:25][CH:26]=[CH:27][N:28]=4)=[CH:20][C:19]=3[CH2:29]O)=[CH:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:10])=[N:4][O:5][C:6]=1[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:57]>CN(C=O)C.O>[Br:57][CH2:29][C:19]1[CH:20]=[C:21]([C:24]2[O:25][CH:26]=[CH:27][N:28]=2)[CH:22]=[CH:23][C:18]=1[C:13]1[C:12]([S:9]([N:8]([C:3]2[C:2]([CH3:1])=[C:6]([CH3:7])[O:5][N:4]=2)[CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])(=[O:11])=[O:10])=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15895427HCID 15895427, compound

Product 1

HCID 15895428HCID 15895428, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the title compound of step E (0.37 g, 072 mmol) in 5 mL of DMF at 5° C., triphenylphosphine (0.283 g, 1.08 mmol) and carbon tetrabromide (0.358 g, 1.08 mmol) were added and the mixture stirred for 5 hours. The solution was then diluted with 100 mL of water and the aqueous solution was extracted with 3×100 mL of EtOAc. The combined organic extracts were then washed once with water and dried and evaporated. The residue thus obtained was chromatographed on 20 g of silica gel using 2:1 hexane:EtOAc to afford 0.285 g (69%) of the title compound of this step.

Workup

  1. extractionthe aqueous solution was extracted with 3×100 mL of EtOAc
  2. washThe combined organic extracts were then washed once with water
  3. customdried
  4. customevaporated
  5. customThe residue thus obtained
  6. customwas chromatographed on 20 g of silica gel using 2:1 hexane

Sources & evidence

ORD record
ord-b9b057af72574b12b9c556d1df4bff0c
Source dataset
uspto-grants-1998_12
Patent number
US05846990

Reaction notes

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