Hydrochloric Acid → Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate

HRID 1988898노트

반응식

HRID 1988898 반응식
[Na].[Br:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:5]([N+]([O-])=O)[CH:4]=1.[N:17](OCCC(C)C)=[O:18].[O-][CH2:26]C.[Na+].Cl>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]([C:10]([O:12][CH2:13][CH3:26])=[O:11])=[N:17][O:18][C:5]=2[CH:4]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 15740598Methyl 4-bromo-2-nitrophenylacetate2회

생성물 1

HCID 53401270Ethyl 6-bromobenzo[d]isoxazole-3-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매2회

실험 절차

Sodium metal (0.09 g) was dissolved in absolute ethanol (2 ml) under nitrogen. A solution of methyl (4-bromo-2-nitrophenyl)acetate (Intermediate 54) (1.0 g) in ethanol (8 ml) was treated with isoamyl nitrite (0.6 ml) followed by the solution of sodium ethoxide, yielding a black mixture. The mixture was stirred at 60° for 90 min then left at room temp. for 18 h. 2N Hydrochloric acid (20 ml) was added and the mixture was extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water (×2) and brine, dried using a hydrophobic filter tube and concentrated under vacuum. The residue was purified on a Varian Bond-Elut SPE cartridge eluting with cyclohexane:ethyl acetate (100:0 to 97:3) to give the title compound as a cream coloured solid (577 mg).

후처리

  1. customyielding a black mixture
  2. waitthen left at room temp. for 18 h
  3. extractionthe mixture was extracted with ethyl acetate (2×20 ml)
  4. washThe combined organic extracts were washed with water (×2) and brine
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a Varian Bond-Elut SPE cartridge
  8. washeluting with cyclohexane:ethyl acetate (100:0 to 97:3)

출처 및 근거

ORD 기록
ord-d251541eadcd449784f138909371131b
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642276B2

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