Bis(2-bromoethyl) ether → HCID 22605547, compound

HRID 2307433Notes

Reaction equation

HRID 2307433 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]([OH:11])[CH3:10])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[F:8][C:7]1[CH:6]=[CH:5][C:4]([CH:9]([OH:11])[CH3:10])=[CH:3][C:2]=1[N:1]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 226055413-Amino-4-fluoro-α-methylbenzenemethanol

Product 1

HCID 22605547HCID 22605547, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(3-amino-4-fluoro-phenyl)ethanol (3.1 g), bromoethyl ether (5.413 g), and i-Pr2NEt (6.1921 g) in toluene (15 mL) was refluxed for 4 hours. After cooling, the reaction mixture was quenched with water. The aqueous layer was extracted with dichloromethane, and the combined organic layers were dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane) to give 3.98 g of the title compound as an oil.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched with water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialthe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel flash chromatography (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-c638bd0c79c9414f890839619f9db694
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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