Iodine → HCID 88096091, compound

HRID 1108180Notes

Reaction equation

HRID 1108180 reaction equation
[C:1]([O:5][CH2:6][CH2:7][C:8]1([CH2:34][CH2:35][O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[S:12][C:11]2[CH:13]=[C:14]3[S:18][C:17]([CH2:26][CH2:27][O:28][C:29]([CH3:32])([CH3:31])[CH3:30])([CH2:19][CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:16][C:15]3=[CH:33][C:10]=2[S:9]1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[I:46]I.S(=O)(O)[O-].[Na+]>CCCCCC.O1CCCC1>[C:29]([O:28][CH2:27][CH2:26][C:17]1([CH2:19][CH2:20][O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[S:18][C:14]2[C:13]([I:46])=[C:11]3[S:12][C:8]([CH2:34][CH2:35][O:36][C:37]([CH3:40])([CH3:39])[CH3:38])([CH2:7][CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[S:9][C:10]3=[CH:33][C:15]=2[S:16]1)([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 807IodineHCID 23665763Sodium BisulfiteHCID 88095918HCID 88095918, compoundHCID 178418339Butyllithium

Product 1

HCID 88096091HCID 88096091, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-20 °C

Procedure

A dry flask under argon was charged with 2,2,6,6-tetra(t-butoxyethyl)benzo[1,2-d:4,5-d']bis(1,3)dithiole (60.0 g, 95.08 mmol) and dry tetrahydrofuran (2000 ml). The mixture was cooled to -20° C. and n-Butyl lithium (76 ml of a 2.5M solution in hexane, 0.19 mol) was added over 3 minutes. The mixture was stirred for 20 minutes at -20° C. and then a solution of iodine (120 g, 0.475 mol) in tetrahydrofuran (500 ml) was added. The reaction mixture was poured into an aqueous sodium bisulphite solution and extracted with diethyl ether. The organic phase was washed once with an aqueous solution of sodium bisulphite and once with brine, dried (MgSO4) and evaporated. The product was purified by chromatography on silica gel using a mixture of CH2Cl2 and ethyl acetate as the eluent. Yield: 36.7 g (51 i).

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed once with an aqueous solution of sodium bisulphite and once with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe product was purified by chromatography on silica gel using
  6. additiona mixture of CH2Cl2 and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ed3e6a5c2b3b4ea6afeb52c0327eb2e3
Source dataset
uspto-grants-2000_05
Patent number
US06063360

Reaction notes

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