Trimethylsilyl iodide → HCID 18787958, compound

HRID 2393678Notes

Reaction equation

HRID 2393678 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([B:13]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=2[CH3:31])[C:14]2[C:19]([CH3:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=2[CH3:22])[CH:10]=[C:9]([B:32]([C:42]2[C:47]([CH3:48])=[CH:46][C:45]([CH3:49])=[CH:44][C:43]=2[CH3:50])[C:33]2[C:38]([CH3:39])=[CH:37][C:36]([CH3:40])=[CH:35][C:34]=2[CH3:41])[CH:8]=1.[CH3:51][Si:52](I)([CH3:54])[CH3:53]>CCCCCC.C1COCC1.O>[C:15]1([CH3:22])[CH:16]=[C:17]([CH3:21])[CH:18]=[C:19]([CH3:20])[C:14]=1[B:13]([C:23]1[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=1[CH3:31])[C:11]1[CH:12]=[C:7]([Si:52]([CH3:54])([CH3:53])[CH3:51])[CH:8]=[C:9]([B:32]([C:42]2[C:43]([CH3:50])=[CH:44][C:45]([CH3:49])=[CH:46][C:47]=2[CH3:48])[C:33]2[C:34]([CH3:41])=[CH:35][C:36]([CH3:40])=[CH:37][C:38]=2[CH3:39])[CH:10]=1

Participants

7

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 18787952HCID 18787952, compoundHCID 178418339Butyllithium

Product 1

HCID 18787958HCID 18787958, compoundYield 110.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

6.25 ml (0.01 mol) of a 1.6M solution of butyllithium in hexane are added at -78° C. to a solution of 6.53 g of (0.01 mol) of 1-bromo-3,5-bis(dimesitylboryl)benzene in 50 ml of THF. The mixture is stirred at -78° C. for 1.5 h, and then 2.0 ml (3.0 g; 0.015 mol) of trimethylsilyl iodide are added over the course of 10 minutes. After the mixture has been stirred again at -78° C. for one hour, it is allowed to warm up to room temperature and stirred for about 12 hours. It is then diluted with water and subjected twice to extraction with 50 ml of ethyl acetate each time. Drying over magnesium sulfate and concentration gives 7.15 g of a viscous oil. Following purification by chromatography (hexane, SiO2), 3.7 g (0.0058 mol, i.e. 58% of theory) of the title compound are obtained as a white solid. Physical data are given in Table 1.

Workup

  1. stirringAfter the mixture has been stirred again at -78° C. for one hour
  2. temperatureto warm up to room temperature
  3. stirringstirred for about 12 hours
  4. extractionsubjected twice to extraction with 50 ml of ethyl acetate each time
  5. dry with materialDrying over magnesium sulfate and concentration

Sources & evidence

ORD record
ord-7952bf4bdfa84189b1f395cebae6863c
Source dataset
uspto-grants-1998_09
Patent number
US05807905

Reaction notes

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