Water → 4-Bromomethyl-2-(4-methoxy-phenyl)-thiazole

HRID 415685Notes

Reaction equation

HRID 415685 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH2:14]O)[N:13]=2)=[CH:5][CH:4]=1.P(Br)(Br)[Br:17].O>C1(C)C=CC=CC=1>[Br:17][CH2:14][C:12]1[N:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[S:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 16494948[2-(4-Methoxyphenyl)-1,3-thiazol-4-yl]methanol

Product 1

HCID 594028514-Bromomethyl-2-(4-methoxy-phenyl)-thiazoleYield 91.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of [2-(4-Methoxy-phenyl)-thiazol-4-yl]-methanol (0.12 g, 0.50 mmol) in 3 ml of toluene was added PBr3 (0.078 ml, 0.813 mmol) and the reaction mixture was heated at 120° C. for 20 min under nitrogen atmosphere. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated to get the desired product (0.13 g, 84%).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aab4a1c283334ce2823b4541f83e058e
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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