Hydrochloric Acid → 4-Bromo-6-isopropyl-2-methyl-1H-indene

HRID 605035노트

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HRID 605035 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:15])[CH3:14])[CH:5]=[C:6]2[C:10]=1[C:9](=O)[CH:8]([CH3:12])[CH2:7]2.[BH4-].[Na+].O.Cl>C1COCC1.CO.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:13]([CH3:14])[CH3:15])[CH:5]=[C:6]2[C:10]=1[CH:9]=[C:8]([CH3:12])[CH2:7]2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 121624887-Bromo-5-isopropyl-2-methyl-1-indanone

생성물 1

HCID 121624894-Bromo-6-isopropyl-2-methyl-1H-indene

시약·촉매·용매 2

HCID 1140Toluene용매HCID 21899815MeOH tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of 22.2 g (83.2 mmol) of 7-bromo-5-isopropyl-2-methyl-1-indanone in 120 ml of THF-methanol (2:1, vol.), 5.06 g (133 mmol) of NaBH4 was added with vigorous stirring over 3 h at 0° C. This mixture was stirred overnight at room temperature; then, 300 ml of cold water was added, and the resulting mixture was acidified with 1 M HCl to pH 1. The organic layer was separated, and the aqueous layer was extracted with 3×150 ml of dichloromethane. The combined organic fractions were dried over K2CO3 and evaporated to dryness, and 200 ml of toluene was added to the yellowish oil obtained. This toluene solution was treated with a catalytic amount of pTolSO3H (ca. 0.2 g) for 1 h at reflux, cooled to room temperature, and evaporated to dryness. The crude product was purified using flash chromatography on Silica Gel 60 (40-63 μm, d 40 mm, l 400 mm; eluent: hexanes). Yield 19.6 g (94%) of 4-bromo-6-isopropyl-2-methyl-1H-indene.

후처리

  1. stirringThis mixture was stirred overnight at room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with 3×150 ml of dichloromethane
  4. dry with materialThe combined organic fractions were dried over K2CO3
  5. customevaporated to dryness, and 200 ml of toluene
  6. additionwas added to the yellowish oil
  7. customobtained
  8. temperatureat reflux
  9. temperaturecooled to room temperature
  10. customevaporated to dryness
  11. customThe crude product was purified

출처 및 근거

ORD 기록
ord-b2a37f91552b47a8b55de325ebde984c
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910783B2

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