Ammonium Chloride → HCID 54764462, compound

HRID 468562Notes

Reaction equation

HRID 468562 reaction equation
C([Mg]Cl)(C)C.[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-]>C1COCC1.[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

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 149428(+)-EpichlorohydrinHCID 86669853HCID 86669853, compoundHCID 178418918HCID 178418918, compound

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

Conditions

Temperature
0 °C

Procedure

2N i-PrMgCl (26 ml) suspended in THF was added dripwise to the 2,4,5-trifluorobenzene bromide (9.55 g) dissolved in THF (30 ml) at −15° C. for 60 min. CuI (0.72 g) was added thereto at −15° C., and heated to −10° C. (S)-epichlorohydrin (4.1 ml) dissolved in THF (40 ml) was added slowly to the resulting mixture, and stirred at 0° C. for 1 hour. 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 to remove MgSO4. The organic solvent was removed from the filtrate under a reduced pressure to obtain the title compound.

Workup

  1. additionwas added slowly to the resulting mixture
  2. customthe organic layer formed
  3. customthereafter was separated
  4. washThe separated organic layer was washed with 50 ml of satuated saline
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customto remove MgSO4
  8. customThe organic solvent was removed from the filtrate under a reduced pressure

Sources & evidence

ORD record
ord-ff4f5026a2114fe792efa62ee89cf95c
Source dataset
uspto-grants-2014_01
Patent number
US08624026B2

Reaction notes

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