Triethyl phosphite → HCID 86653409, compound

HRID 84980Notes

Reaction equation

HRID 84980 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH2:5]I.[CH2:12]([O:14][P:15]([O:19]CC)[O:16][CH2:17][CH3:18])[CH3:13]>>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[F:10])[CH2:5][P:15](=[O:19])([O:16][CH2:17][CH3:18])[O:14][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 31215Triethyl phosphiteHCID 230261953,4,5-Trifluorobenzyl iodide

Product 1

HCID 86653409HCID 86653409, compound

Conditions

Temperature
135 °C

Procedure

3,4,5-trifluorobenzyl iodide (5.075 g, 22.55 mmol) was combined with triethylphosphite (11.6 mL, 67.7 mmol) and the mixture heated and stirred at 135° C. overnight. The mixture was put under hi-vacuum and heated to 70° C. for 12 hours. The final product was a clear oil (6.10 g, 96% yield). 1H NMR (400.14 MHz, CDCl3) δ 6.93 (m, 2H), 4.07 (quint, J=7.10 Hz, 4H), 3.06 (d, J=21.7 Hz, 2H), 1.28 (t, J=7.05 Hz, 6H). 13C{1H} NMR (100.62 MHz, CDCl3) δ 150.8 (dddd, J=249.7, 9.8, 3.8, 3.8 Hz, 2C), 138.74 (dtd, J=250.6, 15.2, 3.9 Hz), 128.2-127.9 (m), 113.9-113.6 (m, 2C), 62.30 (d, J=6.74 Hz, 2C), 32.93 (d, J=139.8 Hz), 16.20 (d, J=6.01 Hz, 2C). 31P{1H} NMR (202.45 MHz, CDCl3): δ 24.96. Analysis calculated (found) %: C 46.82 (46.72), H 5.00 (4.96). MS (FAB, m/z): 269 (M+, 100%). Exact mass calculated (found) for [M+H]+, m/z): 269.05544 (269.05616).

Workup

  1. temperaturethe mixture heated
  2. temperatureheated to 70° C. for 12 hours

Sources & evidence

ORD record
ord-e98353139bf247ab81b30fc869290391
Source dataset
uspto-grants-2014_09
Patent number
US08846978B2

Reaction notes

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