Bis(2-bromoethyl) ether → HCID 67214498, compound

HRID 2421361Notes

Reaction equation

HRID 2421361 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(C(C)C)CC)(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 853000(R)-4-bromo-alpha-methylbenzylamine

Product 1

HCID 67214498HCID 67214498, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-(+)-1-(4-Bromophenyl)ethylamine (0.98 g), 2,2′-dibromodiethyl ether (1.36 g) and diisopropylethylamine (2.5 ml) were stirred in dimethylformamide (20 ml) under argon at 100° C. for 18 h. The reaction mixture was allowed to cool to room temperature, then partitioned between diethyl ether (50 ml) and water (50 ml). The aqueous phase was extracted further with diethyl ether (50 ml) and the combined organic phases were washed with water (100 ml), dried (MgSO4), concentrated in vacuo, redissolved in toluene and purified by Bondelute® chromatography, eluting with 0-50% ethyl acetate/iso-hexane to give the product as a yellow oil (0.86 g).

Workup

  1. custompartitioned between diethyl ether (50 ml) and water (50 ml)
  2. extractionThe aqueous phase was extracted further with diethyl ether (50 ml)
  3. washthe combined organic phases were washed with water (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. dissolutionredissolved in toluene
  7. custompurified by Bondelute® chromatography
  8. washeluting with 0-50% ethyl acetate/iso-hexane

Sources & evidence

ORD record
ord-f66dfa061bca4c8fac2a1e7384a4a234
Source dataset
uspto-grants-2011_06
Patent number
US07956084B2

Reaction notes

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