Triphenylphosphine → 5-(Bromomethyl)-2-furaldehyde

HRID 336835

Reaction equation

HRID 336835 reaction equation
[OH:1][CH2:2][C:3]1[O:7][C:6]([CH:8]=O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:29]N1C(=O)CCC1=O>ClCCl>[Br:29][CH2:8][C:6]1[O:7][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 2373325-(Hydroxymethyl)furfural

Product 1

HCID 119704915-(Bromomethyl)-2-furaldehydeYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

To a solution of 3.4 g (26.7 mmol) of 5-(hydroxymethyl)furan-2-carboxaldehyde and 7.78 g (29.4 mmol) of triphenylphosphine in 300 ml of dichloromethane at −5° C. are added 5.28 g (29.4 mmol) of N-bromosuccinimide in 10 min. The mixture is stirred at −5° C. for 30 min. The mixture is then concentrated and the residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3) to yield 4.38 g (87%) of 5-(bromomethyl)furan-2-carboxaldehyde in the form of a brown solid.

Workup

  1. concentrationThe mixture is then concentrated
  2. customthe residue is purified by chromatography on silica (cyclohexane/AcOet: 7:3)

Sources & evidence

ORD record
ord-3384ac6afaf846c187cbe481e7a64ad1
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Linked notes

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