Ammonium Chloride → HCID 90070482, compound

HRID 590515Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]3[CH2:13][C:14]([CH3:19])([CH3:18])[CH2:15][C:16](=[O:17])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH:20]([Mg]Cl)=[CH2:21].[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]3[CH2:13][C:14]([CH3:19])([CH3:18])[CH2:15][C:16]([CH:20]=[CH2:21])([OH:17])[C:10]=3[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -30 °C

Procedure

2-(3-Bromophenyl)-6,6-dimethyl-6,7-dihydrobenzo[b]thiophen-4(5H)-one (0.36 g, 1.0 mmol) was dissolved in anhydrous THF (10 mL) and the solution was cooled to −30° C. under a nitrogen atmosphere. Vinyl magnesium chloride (2.8 mL, 1.6 M solution in THF, 5.4 mmol) was added to the ketone portion-wise whilst maintaining the temperature at −30° C. Upon completion of the addition, the reaction was allowed to warm to 25° C. and then stirred for 18 hr. Monitoring of the reaction by LC/MS indicated starting material was still present so further vinyl magnesium chloride (2.8 mL, 1.6 M solution in THF, 5.4 mmol) was added. After 2 hr the solution was treated with saturated aqueous ammonium chloride solution. The product was extracted into ethyl acetate (×3) and this was back extracted with water and saturated brine. The organic extracts were combined, dried (MgSO4), filtered and concentrated in vacuo to afford the title compound (0.43 g, quant.).

Workup

temperaturewhilst maintaining the temperature at −30° C
additionUpon completion of the addition
temperatureto warm to 25° C.
customMonitoring of the reaction by LC/MS
additionwas added
extractionThe product was extracted into ethyl acetate (×3)
extractionthis was back extracted with water and saturated brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bef0abdb9a5d476bb27e8620a7d196f1
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233982B2

Reaction notes

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