Carbon tetrabromide → 4-(2-Bromoethyl)morpholine

HRID 1667735Notes

Reaction equation

HRID 1667735 reaction equation
[N:1]1([CH2:7][CH2:8]O)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:11][CH2:8][CH2:7][N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 611632-Morpholinoethanol

Product 1

HCID 15021014-(2-Bromoethyl)morpholineYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.656 g (5 mmole) of 2-morpholin-4-yl-ethanol and 20 mL of dichloromethane at 0 degrees was added 2.49 g (7.5 mmole) of carbon tetrabromide and then 1.57 g (6 mmole) of triphenylphosphine. The mixture was stirred at ambient temperature overnight. The mixture was concentrated under reduced pressure and 50 mL of hexanes was added. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. Purification of the residue by silica gel chromatography, eluting with ethyl acetate-hexanes (gradient 0:100-30:70) gave 0.580 g of 4-(2-bromo-ethyl)-morpholine as a colorless oil.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and 50 mL of hexanes
  2. additionwas added
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customPurification of the residue by silica gel chromatography
  6. washeluting with ethyl acetate-hexanes (gradient 0:100-30:70)

Sources & evidence

ORD record
ord-ccf0347315a840e0805e50f063e0f93a
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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