Benzene → HCID 178440747, compound

HRID 1780563Notes

Reaction equation

HRID 1780563 reaction equation
C([Si:5]([O:18][C:19]1[CH:24]=[CH:23][C:22](Br)=[CH:21][CH:20]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(C)(C)C.C([Li])[CH2:27][CH2:28][CH3:29].F[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[N:33]=1.[Cl-].[Na+].[CH:41]1C=CC=CC=1>CCCCCC.O1CCCC1.CCOCC>[C:28]([C:23]1[CH:22]=[CH:21][C:20]([C:32]2[N:33]=[C:34]([F:38])[CH:35]=[CH:36][CH:37]=2)=[C:19]([O:18][SiH:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:24]=1)([CH3:27])([CH3:29])[CH3:41]

Participants

9

Reactant 5

HCID 241BenzeneHCID 5234Sodium ChlorideHCID 739342,6-DifluoropyridineHCID 11292808Silane, (4-bromophenoxy)(1,1-dimethylethyl)diphenyl-HCID 178418339Butyllithium

Product 1

HCID 178440747HCID 178440747, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

22.61 g (55.0 mmol) of 4-bromophenyl tert.-butyldiphenylsilyl ether in 40 ml of benzene and 35 ml (55.0 mmol) of a 1.6-molar n-butyllithium solution in hexane are stirred overnight at room temperature under argon and then slowly added dropwise to 4.50 ml (50.0 mmol) of 2,6-difluoropyridine in 40 ml of tetrahydrofuran at 0° C. under argon. After a reaction time of 3 hours at 0° C., sodium chloride solution is added, the resulting mixture is taken up in ether, the organic phase is washed with sodium chloride solution, dried over sodium sulfate, filtered, freed from solvent, and the residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate), giving 6.80 g of 6-(4-tert.-butyldiphenylsilyloxyphenyl)-2-fluoropyridine. ##STR44##

Workup

  1. washthe organic phase is washed with sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customthe residue is purified by chromatography (silica gel, 9:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ba9db1d87cf3478a86a7b3673c7e197c
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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