Carbon Tetrachloride → HCID 178498421, compound

HRID 77772Notes

Reaction equation

[C:1](O)([C:3]([F:6])([F:5])[F:4])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC.[CH3:34][O:35][C:36]([C:38]1[CH:39]=[C:40]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)[CH:41]=[C:42]([NH2:44])[CH:43]=1)=[O:37].C(Cl)(Cl)(Cl)[Cl:53]>>[CH3:34][O:35][C:36]([C:38]1[CH:39]=[C:40]([C:45]2[CH:50]=[CH:49][C:48]([CH3:51])=[CH:47][CH:46]=2)[CH:41]=[C:42](/[N:44]=[C:1](\[Cl:53])/[C:3]([F:6])([F:5])[F:4])[CH:43]=1)=[O:37]

Participants

Reactant 5

HCID 5943Carbon Tetrachloride

HCID 6422Trifluoroacetic acid

HCID 8471Triethylamine

HCID 11776Triphenylphosphine

HCID 57850917Methyl 5-amino-4'-methylbiphenyl-3-carboxylate

Product 1

HCID 178498421HCID 178498421, compoundYield 60%

Conditions

Temperature: 0 °C

Procedure

A mixture of CF3COOH (5.19 mmol, 398 mL), PPh3 (15.56 mmol, 4.08 g) and NEt3 (6.22 mmol, 868 μL) in 10 mL of CCl4 was stirred at 0° C. for 10 minutes. 5-Amino-4′-methyl-biphenyl-3-carboxylic acid methyl ester (1.5 g, 6.22 mmol) was then added to the reaction mixture and the mixture was heated to reflux for 2 hours. Solvent was removed under reduced pressure and the residue was purified by flash column chromatography, eluting with n-hexane:ethyl acetate (10:1), giving the 5-[1-chloro-2,2,2-trifluoro-eth-(Z)-ylideneamino]-4′-methyl-biphenyl-3-carboxylic acid methyl ester as light yellow oil (1.3 g, 60% yield).

Workup

temperaturethe mixture was heated
temperatureto reflux for 2 hours
customSolvent was removed under reduced pressure
customthe residue was purified by flash column chromatography
washeluting with n-hexane:ethyl acetate (10:1)

Sources & evidence

ORD record: ord-7849dbc1452942e1a7106e45e9a31a5c
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841336B2

Reaction notes

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