Boron tribromide → 4-Isopropyl-6-hydroxysaccharin

HRID 129041

반응식

HRID 129041 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

HCID 100373464-Isopropyl-6-hydroxysaccharin수율 96%

실험 절차

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.

후처리

  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 vacuo

출처 및 근거

ORD 기록
ord-a73040ecc88e4dcdaf4d2ee90b6ec695
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05466701

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