Phosphorus tribromide → HCID 24899466, compound

HRID 602724Notes

Reaction equation

HRID 602724 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:4][C:3]=1[CH2:24][CH2:25]OC.P(Br)(Br)[Br:29]>C(Cl)(Cl)Cl>[Br:29][CH2:25][CH2:24][C:3]1[CH:4]=[C:5]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 24951165HCID 24951165, compound

Product 1

HCID 24899466HCID 24899466, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-(4-fluoro)phenyl-3-(2-hydroxyethyl)-2-methyl-5-[4-methylsulphonyl)phenyl]-1H-pyrrole (example 23) (1.30 mmol) in CHCl3, PBr3 (5 mL) was added. The resulting mixture was stirred at r.t. for 2 h. The solution was cooled, the reaction quenched with ice, and the mixture basified with a saturated Na2CO3 solution and then extracted with CH2Cl2. The organic phase was washed to neutrality with brine, dried and evaporated under reduced pressure. The residue, purified by flash-chromatography (EtOAc/hexane 4:6 v/v), gave the expected compound as yellow oil (yield 36%) 1H-NMR (CDCl3) δ ppm: 2.03 (s, 3H), 2.96-3.06 (m, 5H), 3.52 (t, 2H, J=7.5), 6.41 (s, 1H), 7.05-7.15 (m, 6H), 7.61-7.66 (m, 2H).

Workup

  1. temperatureThe solution was cooled
  2. customthe reaction quenched with ice
  3. extractionextracted with CH2Cl2
  4. washThe organic phase was washed
  5. customdried
  6. customevaporated under reduced pressure
  7. customThe residue, purified by flash-chromatography (EtOAc/hexane 4:6 v/v)

Sources & evidence

ORD record
ord-f6fbd568ac854daaafc329568278b989
Source dataset
uspto-grants-2011_03
Patent number
US07906551B2

Reaction notes

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