Hydrochloric Acid → 2,3-Dihydro-4-iodo-5-phenylbenzofuran

HRID 617410노트

반응식

HRID 617410 반응식
[C:1]1([C:7]2[C:15](N)=[C:11]3[CH2:12][CH2:13][O:14][C:10]3=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.N([O-])=O.[Na+].[I-:22].[K+]>O.[Cl-].[Na+].O.CCOCC>[I:22][C:15]1[C:11]2[CH2:12][CH2:13][O:14][C:10]=2[CH:9]=[CH:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 218521822,3-Dihydro-5-phenyl-4-benzofuranamineHCID 23668193Sodium Nitrite

생성물 1

HCID 218521872,3-Dihydro-4-iodo-5-phenylbenzofuran수율 57%

시약·촉매·용매 3

HCID 962Water용매2회HCID 3283Diethyl Ether용매HCID 57417360Sodium chloride; water용매

실험 절차

A mechanically stirred solution of 2,3-dihydro-5-phenyl-4-benzofuranamine (1.88 g, 8.90 mmol), ice (~5 g), and concentrated hydrochloric acid (3.9 mL) at 5° C. was treated slowly with a solution of sodium nitrite (0.675 g, 9.78 mmol) in H2O (4 mL). The resulting suspension was stirred 15 min and filtered through a plug of glass wool into a solution of potassium iodide (5.00 g, 30.1 mmol) in H2O. The suspension was allowed to stand for 12 h, treated with Et2O (200 mL) and brine (200 mL), the layers separated, and the aqueous layer further extracted with fresh Et2O (2×300 mL). The combined organic portions were, filtered, washed with 1 N HCl (2×300 mL), brine (200 mL), dried (K2CO3), filtered, and concentrated in vacuo to afford 1.63 g (57%) of the product as a clear oil: 1H NMR (300 MHz, CDCl3) δ 3.23 (t, J=8 Hz, 2H), 4.63 (t, J=8 Hz, 2H), 6.75 (d, J=8 Hz, 1H), 7.02 (d, J=8 Hz, 1H), 7.29-7.42 (m, 5H).

후처리

  1. waitto stand for 12 h
  2. customthe layers separated
  3. extractionthe aqueous layer further extracted with fresh Et2O (2×300 mL)
  4. filtrationfiltered
  5. washwashed with 1 N HCl (2×300 mL), brine (200 mL)
  6. dry with materialdried (K2CO3)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-0762687139e442a1a0b5dfefb19dd8c3
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05948817

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