Triphenylphosphine → HCID 54045525, compound

HRID 234769Notes

Reaction equation

HRID 234769 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][C:5]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[NH:22][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[NH:20][N:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:1][CH2:10][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[NH:22][N:21]([C:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[NH:20][N:19]=2)=[C:4]([Cl:3])[CH:9]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 53978020HCID 53978020, compound

Product 1

HCID 54045525HCID 54045525, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

First 6.79 g of bromine (42.5 mmol) and then 20.4 g of the compound from Example XXXV in 300 ml of methylene chloride are added dropwise to a solution of 11.2 g of triphenylphosphine (42.5 mmol) in 100 ml of methylene chloride under argon in an ice-bath. After the reaction mixture has been stirred at room temperature for 1 hour, it is filtered through silica gel and eluted with methylene chloride. Concentration of the filtrate and digestion of the residue with hexane gives 15.8 g of white crystals [68.9% of theory; melting point 15°-60° C.; Rf 0.40 (hexane/ethyl acetate=3:1)].

Workup

  1. filtrationit is filtered through silica gel
  2. washeluted with methylene chloride

Sources & evidence

ORD record
ord-8ff2eaa15a6d4ac9b38ecc607b9cb205
Source dataset
uspto-grants-1997_01
Patent number
US05596006

Reaction notes

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