Iodine → HCID 118193084, compound

HRID 1775423Notes

Reaction equation

HRID 1775423 reaction equation
C([Li])CCC.[C:6]1([S:12][C:13]2[C:14]3[CH:25]=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]4)=[CH:18][C:15]=3[S:16][CH:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[I:26]I>C1COCC1>[C:6]1([S:12][C:13]2[C:14]3[CH:25]=[C:24]4[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]4)=[CH:18][C:15]=3[S:16][C:17]=2[I:26])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 118192968HCID 118192968, compoundHCID 178418339Butyllithium

Product 1

HCID 118193084HCID 118193084, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under nitrogen atmosphere, n-butyl lithium (1.63 M (solvent: hexane), 0.46 ml, 0.75 mmol) was dripped into a THF solution (5 ml) of 3-(phenylsulfenyl)naphtho[2,3-b]thiophene (146 mg, 0.5 mmol) at 0° C. After the mixture was stirred for 1 hour at room temperature, iodine (190 mg, 0.75 mmol) was added thereto at 0° C. and the mixture was stirred for further 6 hours at room temperature. Subsequently an aqueous solution of Na2S2O5 was added thereto, and the mixture was extracted with CH2Cl2 (50 ml×3) and washed with saline (15 ml×3). The extract liquid was dried with magnesium sulfate, and concentrated. Purification was implemented by column chromatography (silica gel, CHCl3, Rf: 0.9), so that 3-(phenylsulfenyl)-2-iodonaphtho[2,3-b]thiophene was produced as an orange solid (138 mg, 0.3 mmol, yield: 66%).

Workup

  1. stirringat 0° C. and the mixture was stirred for further 6 hours at room temperature
  2. extractionthe mixture was extracted with CH2Cl2 (50 ml×3)
  3. washwashed with saline (15 ml×3)
  4. dry with materialThe extract liquid was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customPurification

Sources & evidence

ORD record
ord-323abc52b11841d6abb5b86350383a74
Source dataset
uspto-grants-2016_02
Patent number
US09260451B2

Reaction notes

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