Triphenylphosphine → 5-(2-bromoethyl)-4-methylthiazole

HRID 633696Notes

Reaction equation

HRID 633696 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[CH:7](O)[CH3:8].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][CH2:7][C:6]1[S:5][CH:4]=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 5817581-(4-Methyl-1,3-thiazol-5-yl)ethan-1-ol

Product 1

HCID 2041875-(2-bromoethyl)-4-methylthiazoleYield 62.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1 g (7 mmol) of 4-methyl-5-thiazolylethanol in 15 mL of dichloromethane is cooled to 0° C. under argon. In a first stage, 1.8 g (7 mmol) of triphenylphosphine are added. Next, 1.30 g (7 mmol) of N-bromosuccinimide are added portionwise over 5 minutes. After stirring for 2 hours at 0° C., the solvent is evaporated off under vacuum. The residue obtained is purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane) to give 900 mg of 5-(2-bromoethyl)-4-methylthiazole, the characteristics of which are as follows:

Workup

  1. customthe solvent is evaporated off under vacuum
  2. customThe residue obtained
  3. customis purified by chromatography on silica gel (eluent: 50/50 EtOAc/heptane)

Sources & evidence

ORD record
ord-1d938bc7b16142089427a1ea97ab4627
Source dataset
uspto-grants-2016_04
Patent number
US09321790B2

Reaction notes

Loading…