Boron tribromide → 4-Isopropyl-6-hydroxysaccharin

HRID 1957430Notes

Reaction equation

HRID 1957430 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]=1

Participants

4

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 101473624-Isopropyl-6-methoxysaccharin

Product 1

HCID 100373464-Isopropyl-6-hydroxysaccharinYield 96%

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 vacua 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

  1. additionWhen addition
  2. temperaturewas heated
  3. temperatureunder reflux for about five hours
  4. temperaturecooled
  5. extractionThe aqueous solution was extracted once with ethyl acetate
  6. extractionExtraction of the mixture with ethyl acetate/diethyl ether (8:2)
  7. customdrying
  8. customthe organic extracts and removal of the solvent in vacua

Sources & evidence

ORD record
ord-5cfd9e2c8937471d8a70b41644b59f84
Source dataset
uspto-grants-1998_07
Patent number
US05783589

Reaction notes

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