Phosphorus tribromide → HCID 66685655, compound

HRID 71270Notes

Reaction equation

HRID 71270 reaction equation
P(Br)(Br)[Br:2].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2([CH2:16][O:17][CH2:18][C:19]3[O:23][N:22]=[C:21]([C:24]4[CH:29]=[CH:28][C:27]([CH2:30]O)=[CH:26][CH:25]=4)[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1>>[Br:2][CH2:30][C:27]1[CH:28]=[CH:29][C:24]([C:21]2[N:20]=[C:19]([CH2:18][O:17][CH2:16][C:12]3([C:9]4[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][CH:8]=4)[CH2:15][CH2:14][CH2:13]3)[O:23][N:22]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 24614Phosphorus tribromideHCID 66693065HCID 66693065, compound

Product 1

HCID 66685655HCID 66685655, compoundYield 94.5%

Procedure

Phosphorous tribromide (30 μL, 323 μmol) was added to a stirred solution of crude (4-(5-(((1-(4-chlorophenyl)cyclobutyl)methoxy)methyl)-1,2,4-oxadiazol-3-yl)phenyl)methanol (83 mg, 215 μmol) at 0° C. The ice bath was removed and stirring was continued for 16 h. The reaction mixture was diluted with dichloromethane and water. The dichloromethane extract was washed with satd. Aqueous NaHCO3 solution, brine, dried (Na2SO4), filtered, and evaporated under reduced pressure to obtain crude 3-(4-(bromomethyl)phenyl)-5-(((1-(4-chlorophenyl)cyclobutyl)methoxy)methyl)-1,2,4-oxadiazole (91 mg, 95% crude yield). LC/MS: m/e 448.92 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. additionThe reaction mixture was diluted with dichloromethane and water
  3. extractionThe dichloromethane extract
  4. washwas washed with satd
  5. dry with materialAqueous NaHCO3 solution, brine, dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f99dde26d8e249258dc7915b32aea62b
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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