Phosgene → 3-[2-Fluoro-5-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride

HRID 2371727Notes

Reaction equation

[C:1]([Cl:4])(Cl)=[O:2].C(=O)([O-])[O-].[K+].[K+].C1(C(C2C=CC=CC=2)[N:18]2[CH2:21][CH:20]([O:22][C:23]3[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=3[F:33])[CH2:19]2)C=CC=CC=1>C(Cl)Cl>[F:33][C:24]1[CH:25]=[CH:26][C:27]([C:29]([F:30])([F:32])[F:31])=[CH:28][C:23]=1[O:22][CH:20]1[CH2:19][N:18]([C:1]([Cl:4])=[O:2])[CH2:21]1

Participants

Conditions

Temperature: 5 °C

Procedure

A mixture of 10.8 g (0.11 mole) of phosgene and 14.2 g (0.11 mole) of potassium carbonate in 200 mL of methylene chloride was cooled to 5° C. in an ice bath while stirring undr nitrogen. After 30 min, the reaction mixture was treated with 40 g (0.1 mole) of 1-(diphenylmethyl)-3-[2-fluoro-5-(trifluoromethyl)phenoxy]azetidine in 100 mL of methylene chloride added dropwise. After stirring for 16 h, the reaction mixture was treated with small pieces of ice to destroy any excess phosgene. Then the reaction mixture was decanted from the inorganic paste and concentrated in vacuo to give 48.6 g of pale yellow oil. The residual oil was distilled at 0.15 mmHg to yield 3 fractions: #1, 12.7 g at 120°-128°; #2, 1.5 g at 128°, and #3 at 128°-132°; with total yield of 19.7 g (66.2%). A sample of fraction #2 was submitted for analysis.

Workup

additionadded dropwise
stirringAfter stirring for 16 h
additionthe reaction mixture was treated with small pieces of ice
customto destroy any excess phosgene
customThen the reaction mixture was decanted from the inorganic paste
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-1f2211643d4d4312b70bea3b5be5d3b9
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05095014

Reaction notes

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