Triphenylphosphine → 7-(2-Bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthalene

HRID 252412Notes

Reaction equation

HRID 252412 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:15]=1[CH:14]=[C:13]([CH2:16][CH:17]([CH:20]([CH3:22])[CH3:21])[CH2:18]O)[CH:12]=[CH:11]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:42]N1C(=O)CCC1=O>ClCCl>[Br:42][CH2:18][CH:17]([CH:20]([CH3:22])[CH3:21])[CH2:16][C:13]1[CH:14]=[C:15]2[C:10]([CH:9]=[CH:8][CH:7]=[C:6]2[O:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 668884672-[8-(2-Methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutan-1-ol

Product 1

HCID 668884037-(2-Bromomethyl-3-methylbutyl)-1-(2-methoxyethoxy)naphthalene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.30 g of 2-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-3-methylbutan-1-ol in 10 ml of dichloromethane at 0° C. is admixed with 0.29 g of triphenylphosphine and 0.20 g of N-bromosuccinimide. After 4 hours, the reaction mixture is concentrated by evaporation to a volume of approx. 3 ml, diluted with hexane, clarified by filtration and then concentrated fully by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. customat 0° C.
  2. concentrationthe reaction mixture is concentrated by evaporation to a volume of approx. 3 ml
  3. additiondiluted with hexane
  4. filtrationclarified by filtration
  5. concentrationconcentrated fully by evaporation

Sources & evidence

ORD record
ord-b0cdfbe227d847f8a1bc8e596a5faeeb
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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