Triphenylphosphine → 3-(Bromomethyl)-5-chlorobenzamide

HRID 1260867Notes

Reaction equation

HRID 1260867 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.[Cl:22][C:23]1[CH:24]=[C:25]([CH:29]=[C:30]([CH2:32]O)[CH:31]=1)[C:26]([NH2:28])=[O:27]>C(#N)C>[Br:20][CH2:32][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([Cl:22])[CH:31]=1)[C:26]([NH2:28])=[O:27]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 24408BromineHCID 589629763-Chloro-5-(hydroxymethyl)benzamide

Product 1

HCID 686616453-(Bromomethyl)-5-chlorobenzamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(Step 2) Triphenylphosphine (1.27 g) was suspended in acetonitrile (50 ml), bromine (0.25 ml) was added, and the suspension was stirred for 30 min. 3-Chloro-5-(hydroxymethyl)benzamide (0.90 g) obtained in Step 1 was added to the reaction mixture, and the mixture was stirred at 85° C. for 2 hr. The reaction solution was quenched with water and extracted with ethyl acetate. The extract was washed with aqueous sodium hydrogen carbonate solution and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1) to give 3-(bromomethyl)-5-chlorobenzamide (0.54 g).

Workup

  1. stirringthe mixture was stirred at 85° C. for 2 hr
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous sodium hydrogen carbonate solution
  5. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. additionthe obtained residue was treated by silica gel chromatography (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-ab3beec7dcf5469a9993f80f73a39ff2
Source dataset
uspto-grants-2013_06
Patent number
US08470859B2

Reaction notes

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