Water → methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-hydroxybenzoate

HRID 1487074Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([O:23]C)=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[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]([CH2:25][CH:26]([CH3:28])[CH3:27])[S:10]([C:13]1[CH:14]=[CH:15][C:16]([OH:23])=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19])(=[O:12])=[O:11]

Participants

Conditions

Temperature: -78 °C

Procedure

Methyl 5-(N-(2,4-dimethylphenyl)-N-isobutylsulfamoyl)-2-methoxybenzoate (1.485 g, 3.66 mmol) was dissolved in dichloromethane (DCM) (10 mL) and this was cooled to −78° C. A solution of boron tribromide in DCM (1M, 18.31 mL, 18.31 mmol) was then added dropwise and the reaction stirred under nitrogen. The reaction was then allowed to warm to room temperature and stirred overnight. Water (20 mL) was added dropwise to the reaction mixture and the crude product extracted to the organic phase of an aqueous work up between DCM and water. The aqueous phase was washed twice with DCM. The organic phase was then dried and concentrated in vacuo to give the crude product. LCMS [LCMS2] Rt 1.42 min, m/z (ES+) 392 (M+H).

Workup

temperatureto warm to room temperature
stirringstirred overnight
extractionthe crude product extracted to the organic phase of an aqueous work up between DCM and water
washThe aqueous phase was washed twice with DCM
customThe organic phase was then dried
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-05a66b9b55054b119c792b705211e1fe
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428452B2

Reaction notes

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