Water → (3,3,4,4,5,5,6,6,6-Nonafluorohexyl)phosphonic acid
Reaction equation
C[Si](Br)(C)C.C([O:8][P:9]([CH2:14][CH2:15][C:16]([F:28])([F:27])[C:17]([F:26])([F:25])[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])(=[O:13])[O:10]CC)C.O>C(Cl)Cl>[F:28][C:16]([F:27])([C:17]([F:25])([F:26])[C:18]([F:23])([F:24])[C:19]([F:21])([F:22])[F:20])[CH2:15][CH2:14][P:9](=[O:8])([OH:13])[OH:10]Participants
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.
Workup
- customwhich was isolated by fractional distillation (90-95% yield)
- customVolatiles were removed in vacuo
Sources & evidence
- ORD record
- ord-1511276d36784ad98b98a4c5d4662359
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000078B2
Reaction notes
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