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

HRID 617410Notes

Reaction equation

HRID 617410 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0762687139e442a1a0b5dfefb19dd8c3
Source dataset
uspto-grants-1999_09
Patent number
US05948817

Reaction notes

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