1,2-Dibromoethane → HCID 54764462, compound

HRID 468560Notes

Reaction equation

HRID 468560 reaction equation
[Mg].BrCCBr.[Br-].[F:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][CH:9]=1.[CH2:16]([C@H:18]1[O:20][CH2:19]1)[Cl:17].[NH4+].[Cl-]>O1CCCC1.[Cu]I.C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([F:15])=[CH:10][C:9]=1[CH2:19][C@H:18]([OH:20])[CH2:16][Cl:17]

Participants

9

Reactant 5

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 149428(+)-EpichlorohydrinHCID 5462224MagnesiumHCID 86669853HCID 86669853, compound2×

Product 1

HCID 54764462HCID 54764462, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

Magnesium (Mg) (1.26 g) was suspended in tetrahydrofuran (THF) (10 ml), and a drop of 1,2-dibromoethane was added thereto. To the resulting mixture, 2,4,5-trifluorobenzene bromide (0.55 g) was added dropwise slowly and then stirred for 30 min. 2,4,5-trifluorobenzene bromide (9.0 g) dissolved in THF (50 ml) was added slowly dropwise to the resulting mixture for 30 min and then stirred at room temperature for 1 hour. CuI (0.72 g) was added to the resulting mixture and the reaction temperature was cooled to 0° C. (S)-epichlorohydrin (4.1 ml) dissolved in THF (40 ml) was added dropwise to the resulting mixture slowly over 30 min, heated to room temperature, and stirred for 2 hours. Satuated NH4Cl (50 ml) and ethyl acetate (50 ml) were added to the resulting mixture, and the organic layer formed thereafter was separated. The separated organic layer was washed with 50 ml of satuated saline, dried over MgSO4, and filtered. The organic solvent was removed from the filtrate under a reduced pressure to obtain the title compound.

Workup

  1. additionwas added slowly dropwise to the resulting mixture for 30 min
  2. stirringstirred at room temperature for 1 hour
  3. additionwas added dropwise to the resulting mixture slowly over 30 min
  4. stirringstirred for 2 hours
  5. customthe organic layer formed
  6. customthereafter was separated
  7. washThe separated organic layer was washed with 50 ml of satuated saline
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customThe organic solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-d279b29a4cec4792b2694db03f48b2b6
Source dataset
uspto-grants-2014_01
Patent number
US08624026B2

Reaction notes

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