Heptafluorobutyryl Chloride → Heptafluorobutyraldehyde

HRID 36464

Reaction equation

C([SiH](C(C)C)C(C)C)(C)C.[C:11]([C:15]([C:18]([C:21](Cl)=[O:22])([F:20])[F:19])([F:17])[F:16])([F:14])([F:13])[F:12]>[Pd]>[C:18]([CH:21]=[O:22])([C:15]([C:11]([F:12])([F:13])[F:14])([F:17])[F:16])([F:20])[F:19]

Participants

Conditions

Temperature: 0 °C

Procedure

A 3-necked round bottom flask fitted with dropping funnel, dry-ice condenser, and gas inlet was charged with 10% Pd/C(0.35 g) and cooled to 0° C. Triisopropylsilane (7.29 g, 46 mmol) was added, and CF3CF2CF2C(O)Cl (9.30 g, 40 mmol) was added dropwise over a 10 min period. The reactor was connected to a cold trap (-78° C.) while the mixture was stirred for 18 hr. Transfer from the trap and reaction vessel gave a total of 5.1 g (62%) of colorless liquid. 1H NMR (CD2Cl2): 9.62 (m). 19F NMR: -81.24 (t, J=8.3 Hz), -126.4 (quartet of doublets, Jq =8.3, Jd =3.2), -127.9 (s).

Workup

customA 3-necked round bottom flask fitted
customThe reactor was connected to a cold trap
customTransfer from the trap and reaction vessel

Sources & evidence

ORD record: ord-10a3cd1bb37642bd9b0560357400337e
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05414140

Linked notes

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