Dichloromethane → (1,1-Difluoro-pentadecyl)-phosphonic acid

HRID 1351075Notes

Reaction equation

HRID 1351075 reaction equation
C([O:3][P:4]([C:9]([F:25])([F:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:8])[O:5]CC)C.C(Cl)Cl>>[F:25][C:9]([P:4](=[O:3])([OH:5])[OH:8])([F:24])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 11773544(1,1-Difluoro-pentadecyl)Phosphonic Acid Diethyl Ester

Product 1

HCID 11393306(1,1-Difluoro-pentadecyl)-phosphonic acidYield 78.1%

Procedure

To a solution of vacuum dried 10 (225 mg, 0.585 mmol) in methylene chloride (5 mL) bromotrimethyl silane (895 mg, 5.85 mmol) was added and the mixture was stirred at room temperature. TLC showed completion of the reaction after 6 h. Solvents were removed under reduced pressure, and the residue was stirred in 95% methanol (3 mL) for 1 h. The mixture was concentrated under reduced pressure, dried under vacuum to give 150 mg (78%) of 11 as light yellow solid. mp 66–69° C.; 1H NMR (CD3OD): δ 2.03 (m, 2H), 1.59 (m, 2H), 1.24 (br s, 22H), 0.90 (t, J=6.6 Hz, 3H); MS: [M−H]— at m/z 327.3. Anal. (C15H31F2O3P.0.2H2O) C, H.

Workup

  1. additionwas added
  2. customcompletion of the reaction after 6 h
  3. customSolvents were removed under reduced pressure
  4. stirringthe residue was stirred in 95% methanol (3 mL) for 1 h
  5. concentrationThe mixture was concentrated under reduced pressure
  6. customdried under vacuum

Sources & evidence

ORD record
ord-88f571bfe6864a57a745350a174982b2
Source dataset
uspto-grants-2007_05
Patent number
US07217704B2

Reaction notes

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