Boron tribromide → 4-Isopropyl-6-hydroxysaccharin
Reaction equation
[CH:1]([C:4]1[CH:14]=[C:13]([O:15]C)[CH:12]=[C:11]2[C:5]=1[C:6](=[O:17])[NH:7][S:8]2(=[O:10])=[O:9])([CH3:3])[CH3:2].B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>>[OH:15][C:13]1[CH:12]=[C:11]2[C:5]([C:6](=[O:17])[NH:7][S:8]2(=[O:10])=[O:9])=[C:4]([CH:1]([CH3:3])[CH3:2])[CH:14]=1Participants
Procedure
To a solution of 1.0 g (0.0039 mol) of 4-isopropyl-6-methoxysaccharin in 15 ml of MDC was added at ambient temperature 1.28 g (5.12 ml) of a 1M solution of boron tribromide in MDC. When addition was complete the reaction mixture was heated under reflux for about five hours, cooled, taken to dryness in vacuo and the residue treated with ice and saturated sodium bicarbonate. The aqueous solution was extracted once with ethyl acetate and then acidified to pH 1 with concentrated hydrochloric acid. Extraction of the mixture with ethyl acetate/diethyl ether (8:2), drying the organic extracts and removal of the solvent in vacuo afforded 0.9 g (96%) of 6-hydroxy-4-isopropylsaccharin as a white crystalline solid which was used as such in the next step.
Workup
- additionWhen addition
- temperaturewas heated
- temperatureunder reflux for about five hours
- temperaturecooled
- extractionThe aqueous solution was extracted once with ethyl acetate
- extractionExtraction of the mixture with ethyl acetate/diethyl ether (8:2)
- customdrying
- customthe organic extracts and removal of the solvent in vacuo
Sources & evidence
- ORD record
- ord-673735cef67d4c3fab9eb501945f08a3
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05563163
Reaction notes
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