Triethyl phosphite → Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

HRID 928123Notes

Reaction equation

HRID 928123 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH2:7]Br)=[N:4][CH:3]=1.[P:9]([O:16]CC)([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12]>C1(C)C=CC=CC=1>[CH2:11]([O:10][P:9]([CH2:7][C:5]1[S:6][C:2]([Br:1])=[CH:3][N:4]=1)(=[O:16])[O:13][CH2:14][CH3:15])[CH3:12]

Participants

4

Reactant 2

HCID 31215Triethyl phosphiteHCID 594709305-Bromo-2-(bromomethyl)-1,3-thiazole

Product 1

HCID 86720195Diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2-(bromomethyl)-1,3-thiazole (1.02 g, 3.97 mmol) and triethyl phosphite (1.389 mL, 7.94 mmol) were combined in toluene (8 mL) and stirred at reflux overnight. The reaction was cooled to room temperature and concentrated in vacuo. The residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate) to afford diethyl[(5-bromo-1,3-thiazol-2-yl)methyl]phosphonate as a yellow oil. MS ESI calc'd. for C8H14BrNO3PS [M+H]+ 314, 316. found 314, 316. 1H NMR (500 MHz, CDCl3) δ 7.59 (s, 1H), 4.17-4.09 (m, 4H), 3.57 (d, J=21.2 Hz, 2H), 1.32 (t, J=7.1 Hz, 6H).

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel (0-5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-bef95277b735410194c9b8f242854e50
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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