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

HRID 617410ノート

反応式

HRID 617410 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 218521872,3-Dihydro-4-iodo-5-phenylbenzofuran収率 57%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 3283Diethyl Ether溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0762687139e442a1a0b5dfefb19dd8c3
出典データセット
uspto-grants-1999_09
特許番号
US05948817

反応ノート

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