Water → HCID 86731581, compound

HRID 1746402Notes

Reaction equation

HRID 1746402 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 twice with DCM (20 mL×2). 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 column chromatography (20 mins, 20 g, 0-25% EtOAc in cyclohexane). The relevant fractions were then combined and condensed, to give the product, N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide, 384.4 mg.

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 twice with DCM (20 mL×2)
  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 column chromatography (20 mins, 20 g, 0-25% EtOAc in cyclohexane)
  9. customcondensed

Sources & evidence

ORD record
ord-37967077b52349489ad82e8d6eea1962
Source dataset
uspto-grants-2015_10
Patent number
US09150508B2

Reaction notes

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