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

HRID 2421364Notes

Reaction equation

HRID 2421364 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-dd756f4bd77f4166b820104ff4ec3a5a
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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