Phosphorus tribromide → 4-(Bromomethyl)-2-((2-methoxyethoxy)methyl)thiazole

HRID 1424345Notes

Reaction equation

HRID 1424345 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][C:7]1[S:8][CH:9]=[C:10]([CH2:12]O)[N:11]=1.P(Br)(Br)[Br:15]>CCOCC.C(OCC)(=O)C>[Br:15][CH2:12][C:10]1[N:11]=[C:7]([CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[S:8][CH:9]=1

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 86700892(2-((2-Methoxyethoxy)methyl)thiazol-4-yl)methanol

Product 1

HCID 867008934-(Bromomethyl)-2-((2-methoxyethoxy)methyl)thiazoleYield 82.6%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2-((2-methoxyethoxy)methyl)thiazol-4-yl)methanol (0.35 g, 1.72 mmol) in ether (15 mL) was treated with PBr3 (0.1 mL, 1.06 mmol) at RT. There is formation of a precipitate. The reaction was stirred at RT for 18 hours, then diluted with ethyl acetate and washed with sat. NaHCO3 (1×) and brine (1×), dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (3×10 cm, 20% ethyl acetate/CH2Cl2) to give the title material (0.233 g, 51%) as a clear oil. 1H NMR (CDCl3, 400 MHz) δ ppm: 7.27 (s, 1H), 4.83 (s, 2H), 4.55 (s, 2H), 3.73-3.76 (m, 2H), 3.57-3.60 (m, 2H), 3.39 (s, 3H).

Workup

  1. washwashed with sat. NaHCO3 (1×) and brine (1×)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (3×10 cm, 20% ethyl acetate/CH2Cl2)

Sources & evidence

ORD record
ord-a7f1a53dd1d047cb9ff2ee56b27936dc
Source dataset
uspto-grants-2015_01
Patent number
US08927688B2

Reaction notes

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