Triethyl phosphite → HCID 20208637, compound

HRID 542418Notes

Reaction equation

HRID 542418 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br.[CH2:13]([O:15][P:16]([O:20]CC)[O:17][CH2:18][CH3:19])[CH3:14]>>[Br:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][P:16](=[O:20])([O:17][CH2:18][CH3:19])[O:15][CH2:13][CH3:14]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 202086332-(3-Bromopropyl)benzyl bromide

Product 1

HCID 20208637HCID 20208637, compoundYield 83%

Procedure

In a round bottom flask equipped for distillation, 11.36 g (38.9 mmol) of 2-(3-bromopropyl)benzyl bromide and 6.46 (38.9 mmol) of freshly distilled triethylphosphite were heated with stirring at 100°-110° C. on an oil bath. When ethyl bromide ceased distilling off (about 2 h) the remaining volatile by-products and the triethylphosphite were removed from the mixture by distillation under vacuum. The remaining oil was chromatographed on a column of silica gel with hexame-ethyl acetate (1:1) as eluant. The combined fractions were concentrated under reduced pressure to yield 11.2 g (83%) of the product as a clear oil. IR(neat): 2985, 1496, 1450, 1391, 1252, 1162, 104, 967, 843, 802, 758 cm-1. 1H NMR(CDCl3) δ 1.2 (t, 6); 1.8-2.3 (m, 2H); 2.7-3.55 (m, 4H); 3.8-4.2 (m, 2H); 7.1-7.4 (m, 4H).

Workup

  1. temperaturewere heated
  2. distillationWhen ethyl bromide ceased distilling off (about 2 h) the remaining volatile by-products
  3. customthe triethylphosphite were removed from the mixture by distillation under vacuum
  4. customThe remaining oil was chromatographed on a column of silica gel with hexame-ethyl acetate (1:1) as eluant
  5. concentrationThe combined fractions were concentrated under reduced pressure

Sources & evidence

ORD record
ord-534c0d146add497797903aa8ddf66e08
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

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