Iodine → HCID 15337859, compound

HRID 1600591Notes

Reaction equation

HRID 1600591 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][C:14]2[C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[I:30]I>O1CCCC1>[I:30][C:18]1[S:17][C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[C:14]=1[O:13][C:12]1[CH:23]=[CH:24][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 807IodineHCID 15347456HCID 15347456, compoundHCID 178418339Butyllithium

Product 1

HCID 15337859HCID 15337859, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 3-(4-benzyloxyphenoxy)benzo[b]thiophene (6.00 g, 18.1 mmol) in anhydrous tetrahydrofuran (100 mL) under N2 at -78° C. was added n-butyllithium (12.4 mL, 19.9 mmol, 1.6 M in hexanes) dropwise via syringe. The solution turned from colorless to deep orange. After stirring for 20 minutes at -78° C., the lithio species was treated with I2 (5.03, 19.9 mmol), added dropwise via canula as a solution in 50 mL of anhydrous tetrahydrofuran. Upon completion of the addition, the reaction turned light yellow in color, and was allowed to slowly warm to room temperature. The reaction was quenched by the addition of 0.1 N sodium sulfite solution (200 mL). The layers were separated and the aqueous extracted with ethyl acetate (2×150 mL). The organic layers were combined, dried (sodium sulfate), and concentrated in vacuo to give an oil that crystallized on standing. Recrystallization from hexanes/ethyl ether yielded 7.10 g (86%) of 2-iodo-3-(4-benzyloxyphenoxy)benzo[b]thiophene as a white crystalline powder. mp 87-92° C. 1H NMR (CDCl3) d 7.72 (d, J=8.1 Hz, 1H), 7.47-7.20 (m, 8H), 6.89 (s, 4H), 5.01 (s, 2H). Anal. Calcd. for C21H15O2SI: C, 55.03; H, 3.30. Found: C, 55.29; H, 3.31.

Workup

  1. additionUpon completion of the addition
  2. temperatureto slowly warm to room temperature
  3. customThe reaction was quenched by the addition of 0.1 N sodium sulfite solution (200 mL)
  4. customThe layers were separated
  5. extractionthe aqueous extracted with ethyl acetate (2×150 mL)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customto give an oil that
  9. customcrystallized
  10. customRecrystallization from hexanes/ethyl ether

Sources & evidence

ORD record
ord-76b80d9865f848f9b1099615c822d50e
Source dataset
uspto-grants-1999_11
Patent number
US05977098

Reaction notes

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