Triethyl Phosphate → Diethyl (3,3,4,4,5,5,6,6,6-nonafluorohexyl)phosphonate
Reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([F:14])([F:13])[C:4]([F:12])([F:11])[C:5]([F:10])([F:9])[CH2:6][CH2:7]I.[P:17](OCC)([O:22][CH2:23][CH3:24])([O:19][CH2:20][CH3:21])=[O:18]>>[CH2:20]([O:19][P:17]([CH2:7][CH2:6][C:5]([F:10])([F:9])[C:4]([F:12])([F:11])[C:3]([F:14])([F:13])[C:2]([F:16])([F:15])[F:1])(=[O:18])[O:22][CH2:23][CH3:24])[CH3:21]Participants
Conditions
- Temperature
- 160 °C
Procedure
Neat 1,1,1,2,2,3,3,4,4-nonafluoro-6-iodohexane (10 mmol) was added to 50 mmol of triethyl phosphate. The reaction mixture was heated at 160° C. overnight to produce diethyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)phosphonate, which was isolated by fractional distillation (90-95% yield). Neat trimethylsilyl bromide (21 mmol) was added slowly to a solution of diethyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)phosphonate (7 mmol) in dry CH2Cl2 (25 mL) at 0° C. The reaction mixture was stirred overnight at room temperature, after which time water (30 mmol) was added to the reaction mixture. Volatiles were removed in vacuo leaving (3,3,4,4,5,5,6,6,6-nonafluorohexyl)phosphonic acid as a white crystal (>95% yield). The procedure for producing the phosphonic acid salt was similar as described for Intermediate 1.
Sources & evidence
- ORD record
- ord-b3917a507b004bc0b888dbb18ef89169
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000078B2
Reaction notes
Loading…