5-Bromo-2-chlorotoluene → HCID 67073213, compound

HRID 2252988Notes

Reaction equation

HRID 2252988 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1.C([Li])(C)(C)C.[CH2:15]([C@@H:17]1[O:19][CH2:18]1)[Cl:16]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:16][CH2:15][C@H:17]([OH:19])[CH2:18][C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6098995-Bromo-2-chlorotolueneHCID 2734062(-)-EpichlorohydrinHCID 178418306HCID 178418306, compound

Product 1

HCID 67073213HCID 67073213, compoundYield 44.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 1.0 g (4.9 mmol) 5-bromo-2-chlorotoluene in 10 mL toluene was cooled down to −70° C. and treated dropwise with 3.6 mL (5.4 mmol; 1.5M solution in toluene) tert-butyllithium. After 30 min. 0.42 mL (5.3 mmol) (R)-(−)-epichlorohydrin was added and the temperature was allowed to rise to 0° C. After 1 h the reaction mixture was diluted with ethyl acetate and extracted with 10% aqueous sodium bicarbonate solution followed by brine. The organic layer was dried over magnesium sulfate, filtered and evaporated and the residue was purified by column chromatography on silica gel with n-hexane:ethyl acetate (1:1) as eluant to give the title compound as a colorless oil (44.8%).

Workup

  1. customto rise to 0° C
  2. extractionextracted with 10% aqueous sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was purified by column chromatography on silica gel with n-hexane:ethyl acetate (1:1) as eluant

Sources & evidence

ORD record
ord-0d6212e0d3854485b5d47a60e7ff37a3
Source dataset
uspto-grants-2008_01
Patent number
US07323466B2

Reaction notes

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