Water → HCID 86731581, compound

HRID 1487033Notes

Reaction equation

HRID 1487033 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19]C)[CH:14]=1)(=[O:12])=[O:11].B(Br)(Br)Br.O>ClCCl>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=1)(=[O:11])=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 86731582HCID 86731582, compound

Product 1

HCID 86731581HCID 86731581, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

N-(2,4-dimethylphenyl)-N-isobutyl-3-methoxybenzenesulfonamide (431.4 mg, 1.242 mmol) was dissolved in dichloromethane (DCM) (10 mL) and cooled to −78° C. BBr3 in DCM (1M) (6.21 mL, 6.21 mmol) was added dropwise and the reaction put under nitrogen. The reaction was allowed to reach room temperature and left to stir overnight. Water (20 mL) was added dropwise into the reaction mixture, until no more fumes were released. The crude product was then extracted to the organic phase of an aqueous work up between DCM (30 mL) and water (20 mL). The aqueous phase was washed with DCM (2×20 mL). The organic phase was then dried and concentrated in vacuo. The crude product was then dissolved in a minimum of DCM, and loaded onto a silica column before being purified by silica (Si) column chromatography (20 minutes, 0-25% EtOAc in cyclohexane). The relevant fractions were then combined and condensed, to give the desired product, 384.4 mg. LCMS [LCMS1] Rt 1.26 min, m/z (ES+) 334 (M+H).

Workup

  1. customto reach room temperature
  2. waitleft
  3. extractionThe crude product was then extracted to the organic phase of an aqueous work up between DCM (30 mL) and water (20 mL)
  4. washThe aqueous phase was washed with DCM (2×20 mL)
  5. customThe organic phase was then dried
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude product was then dissolved in a minimum of DCM
  8. custombefore being purified by silica (Si) column chromatography (20 minutes, 0-25% EtOAc in cyclohexane)
  9. customcondensed

Sources & evidence

ORD record
ord-bdc2c7c019674baea65e75dacde25de2
Source dataset
uspto-grants-2016_08
Patent number
US09428452B2

Reaction notes

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