Triphenylphosphine → Triphenylphosphane dibromide

HRID 371380Notes

Reaction equation

HRID 371380 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20]Br>CN(C)C=O>[Br-:20].[Br-:20].[C:14]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 24408Bromine

Product 1

HCID 12890784Triphenylphosphane dibromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 9.13 g (0.035 mole) of triphenylphosphine in 70 ml of dimethylformamide at 5°-10° C. was slowly added 1.93 ml (0.035 mole) of bromine to form triphenylphosphine dibromide. The yellow-orange mixture was then treated with 1.91 g (0.01 mole) of 2,4-diamino-6-hydroxymethylpyrido[2,3-d]pyrimidine at 10° C. The mixture was stirred for 45 minutes at ambient temperature. The red solution was cooled to 10° C., treated with 1 ml of ethanol (dropwise) and stirred for an hour at ambient temperature. The solution was concentrated to a volume of 10 ml in vacuo and washed thrice with 90-ml portions of warm (40° C.) benzene. The residual liquid was treated with 30 ml of hot acetic acid. The hot solution was filtered and the filtrate chilled to afford 2.44 g of crystalline precipitate; UV λ pH 1 248 nm (ε 20, 200), 320 (8,780), 333 (7,030); λ pH 13 270 (11,050), 342 (6,300 ). Calc'd for C8H8N5Br.HBr: C, 28.7; H, 2.7; N, 20.9; Br, 47.7. Found: C, 28.9; H, 2.85; N, 21.1; Br, 47.4.

Workup

  1. customat 5°-10° C.

Sources & evidence

ORD record
ord-29badc16957b4fd2953731d6c012f1ad
Source dataset
uspto-grants-1985_07
Patent number
US04532241

Reaction notes

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