Diethyl Ether → Benzyl 2-benzyloxymethyl-4-bromobutyl ether

HRID 2291847Notes

Reaction equation

HRID 2291847 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:42]N1C(=O)CCC1=O.CCOCC>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]([CH2:11][CH2:12][Br:42])[CH2:14][O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 5622184-Benzyloxy-3-benzyloxymethylbutanol

Product 1

HCID 15928659Benzyl 2-benzyloxymethyl-4-bromobutyl ether

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzyloxy-3-benzyloxymethylbutan-1-ol (41.75 g, 139 mmol) in 150 ml of dry dichloromethane was cooled in ice-water bath. Triphenylphosphine (42.0 g, 160 mmol) was added with stirring and then N-bromosuccinimide (26.0 g, 146 mmol) in portions during 15 min. After 1 h at room temperature ether (400 ml) was added and the precipitated triphenylphosphine oxide filtered off. The solution was concentrated in vacuum to a small volume, and more ether was added to extract the product from precipitated triphenylphosphine oxide. Finally, this extraction-precipitation step was repeated with light petroleum to give, after evaporation, 33.55 g (66%) of crude title compound.

Workup

  1. filtrationthe precipitated triphenylphosphine oxide filtered off
  2. concentrationThe solution was concentrated in vacuum to a small volume, and more ether
  3. additionwas added
  4. extractionto extract the product
  5. customfrom precipitated triphenylphosphine oxide
  6. customFinally, this extraction-precipitation step
  7. customto give
  8. customafter evaporation, 33.55 g (66%) of crude title compound

Sources & evidence

ORD record
ord-927cc73f510d4a329ef490f0e3ea5e9f
Source dataset
uspto-grants-1989_01
Patent number
US04798833

Reaction notes

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