Myristyl bromide → (1,1-Difluoro-pentadecyl)Phosphonic Acid Diethyl Ester

HRID 550344Notes

Reaction equation

HRID 550344 reaction equation
[F:1][CH:2]([F:11])[P:3]([O:8][CH2:9][CH3:10])(=[O:7])[O:4][CH2:5][CH3:6].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C1COCC1>[CH2:5]([O:4][P:3]([C:2]([F:1])([F:11])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12])(=[O:7])[O:8][CH2:9][CH3:10])[CH3:6]

Participants

4

Reactant 2

HCID 8208Myristyl bromideHCID 2758305Phosphonic acid, (difluoromethyl)-, diethyl ester

Product 1

HCID 11773544(1,1-Difluoro-pentadecyl)Phosphonic Acid Diethyl EsterYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl difluoromethanephosphonate (1.0 g, 5.316 mmol) in THF (50 mL) 2 M LDA (626 mg, 5.847 mmol) was added at −78° C. and stirred for 30 min. Tetradecyl bromide (1.474 g, 5.316 mmol) in THF (10 mL) was added to the mixture at −78° C. and the reaction mixture was stirred overnight. THF was evaporated and the residual oil was purified by flash chromatography using 30% ethyl acetate in hexane as eluent to give 817 mg (40%) of compound 10 as colorless oil. 1H NMR (CDCl3): δ4.26 (m, 4H), 2.05 (m, 2H), 1.56 (m, 2H), 1.37 (t, J=6.9 Hz, 6H), 1.25 (br s, 22H), 0.87 (t, J=6.6 Hz, 3H); MS: [M+23Na] at m/z 407.2.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customTHF was evaporated
  3. customthe residual oil was purified by flash chromatography

Sources & evidence

ORD record
ord-4117f5ade5304ceeb2b3ea1da2f2567e
Source dataset
uspto-grants-2011_05
Patent number
US07947665B2

Reaction notes

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