Carbon tetrabromide → HCID 53747118, compound

HRID 1063939Notes

Reaction equation

HRID 1063939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15]O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:50].[Cl-].[NH4+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[CH2:25][O:26][C:27](=[O:29])[CH3:28])[C@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15][Br:50])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 53964382HCID 53964382, compound

Product 1

HCID 53747118HCID 53747118, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
22 °C

Procedure

To a solution of 4-chloro-N-[5-chloro-2-(acetoxymethyl)phenyl]-N-[(R)-1-methyl-4-hydroxybutyl]benzenesulfonamide (500 mg, 1.09 mmol) in acetonitrile (2 mL) was added triphenylphosphine (571 mg, 2.18 mmol) and carbon tetrabromide (720 mg, 2.18 mmol) at 0° C. The resulting mixture was allowed to stir at 22° C. for 12 h followed by the addition of 25 mL of sat. ammonium chloride. The product was extracted with ether (2×25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure. Silica gel chromatography (1:4 ethyl acetate:hexanes) of the concentrate afforded 479 mg of 4-chloro-N-[5-chloro-2-(acetoxymethyl)phenyl]-N-[(R)-1-methyl-4-bromobutyl]benzenesulfonamide as a colorless oil in 84% yield.

Workup

  1. extractionThe product was extracted with ether (2×25 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-793c86805d5548eea18db9380d625f99
Source dataset
uspto-grants-2005_11
Patent number
US06967196B1

Reaction notes

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