4-Fluorophenyl isothiocyanate → HCID 68488565, compound

HRID 1882348Notes

Reaction equation

[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].C([Li])CCC.[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]=[S:21])=[CH:15][CH:14]=1.[CH:22]1([CH2:28]Br)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1.CCCCCC>[F:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]=[C:20]([S:21][CH2:28][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH2:2][CH2:1][Si:3]([CH3:6])([CH3:5])[CH3:4])=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethynyltrimethylsilane (0.89 g) in THF (15 mL) was added a 1.57M solution (5.0 mL) of n-butyllithium in hexane at −78° C. under a nitrogen atmosphere, and the mixture was stirred at the same temperature for 0.5 hours. After the reaction mixture was warmed to 0° C., a 4-fluorophenyl isothiocyanate (1.30 g) in THF (5 mL) was added dropwise thereto at −78° C. Then, the reaction mixture was slowly warmed to 0° C. At the same temperature, a solution of cyclohexylmethyl bromide (1.52 g) in THF (5 mL) was added dropwise thereto, and the mixture was stirred at 50° C. for 7 hours. The solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain cyclohexylmethyl N-(4-fluorophenyl)-3-(trimethylsilyl)thiopropionimidate (0.38 g) as a brown oil.

Workup

customat −78° C
temperatureThen, the reaction mixture was slowly warmed to 0° C
stirringthe mixture was stirred at 50° C. for 7 hours
distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-0b51f569974145b0abd15f4f902b3226
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318981B2

Reaction notes

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