Bis(2-bromoethyl) ether → HCID 67214317, compound

HRID 1245842Notes

Reaction equation

HRID 1245842 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:11]([O:14][CH2:15][CH2:16]Br)[CH2:12]Br.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:16][CH2:15][O:14][CH2:11][CH2:12]2)[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamine

Product 1

HCID 67214317HCID 67214317, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(1S)-(−)-1-(4-Bromophenyl)ethylamine (2.4 g), 2,2′-dibromodiethylether (3.25 g) and N,N-diisopropylethylamine (6 ml) were heated to 100° C. in dimethylformamide (40 ml) for 18 h, allowed to cool and partitioned between water and ethyl acetate. The organic phase was dried (MgSO4), evaporated under vacuum and purified by column chromatography using a 0–40% ethyl acetate/iso-hexane gradient. The product was obtained as a yellow oil (1.91 g).

Workup

  1. temperatureto cool
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated under vacuum
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-bf4c7b0eecd74d329caace3ad65cb330
Source dataset
uspto-grants-2006_10
Patent number
US07125896B2

Reaction notes

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