Ethyl Bromide → 5-Diethylphosphonomethyl-3-phenylisoxazole

HRID 2248970Notes

Reaction equation

HRID 2248970 reaction equation
Br[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1.[P:14]([O:21]CC)([O:18][CH2:19][CH3:20])[O:15][CH2:16][CH3:17].C(Br)C>>[CH2:16]([O:15][P:14]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1)([O:18][CH2:19][CH3:20])=[O:21])[CH3:17]

Participants

4

Reactant 3

HCID 6332Ethyl BromideHCID 31215Triethyl phosphiteHCID 27487965-(Bromomethyl)-3-phenylisoxazole

Product 1

HCID 542259365-Diethylphosphonomethyl-3-phenylisoxazole

Procedure

5-Bromomethyl-3-phenylisoxazole (7.14 g, 30 mmol) and triethyl phosphite (10.4 ml, 60 mmol) were heated at 150° C. until no more ethyl bromide distilled, then the temperature maintained for a further 1 h. The mixture was then distilled under reduced pressure to give 5-diethylphosphonomethyl-3-phenylisoxazole bp 190°-192° C. at 0.5 mm Hg (8.15 g, 27.6 mmol, 92%); νmax (film) 2980, 2900, 1605, 1580, 1465, 1440, 1410, 1250, 1160, 1020, 970, 770, 690, 670 cm-1 ; δH (CDCl3) 1.30(6H, t, J 7 Hz, OCH2CH3), 3.45(1H, d, JH-P 22 Hz, CH2 -P), 4.10(4H, m, OCH2CH3), 6.55(1H, d, J 3 Hz, CH-4), 7.40(3H, m, Ph), 7.65(2H, m, Ph); δC (CDCl3) 16.3, 16.4(OCH2CH3), 24.7, 26.9(CH2 -P), 62.8, 62.9(OCH2CH3), 101.5, 101.6 (C-4), 126.8, 128.9, 130.0 (Ph), 162.8 (C-3), 164.3, 164.4 (C-2).

Workup

  1. distillationdistilled
  2. temperaturethe temperature maintained for a further 1 h
  3. distillationThe mixture was then distilled under reduced pressure

Sources & evidence

ORD record
ord-0e3be1a38f8942b9aa586a705964d47c
Source dataset
uspto-grants-1991_08
Patent number
US05041567

Reaction notes

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