HCID 59235385, compound → HCID 59235403, compound

HRID 2174329Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:15])=[CH:4][C:5]([Cl:14])=[C:6]([CH:13]=1)[C:7](N(OC)C)=[O:8].[CH2:16]([C:18]1[CH:23]=[CH:22][C:21]([Mg]Br)=[CH:20][CH:19]=1)[CH3:17]>O1CCCC1>[Br:1][C:2]1[C:3]([F:15])=[CH:4][C:5]([Cl:14])=[C:6]([C:7]([C:21]2[CH:22]=[CH:23][C:18]([CH2:16][CH3:17])=[CH:19][CH:20]=2)=[O:8])[CH:13]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 5-bromo-2-chloro-4-fluoro-N-methoxy-N-methylbenzamide (936 mg, 3.17 mmol) in tetrahydrofuran (15 mL) was added (4-ethylphenyl)magnesium bromide (9.5 mmol, 9.5 mL, 1 M in tetrahydrofuran) at 0° C. The mixture was stirred at 25° C. for 1 hour, then the reaction was quenched with saturated ammonium chloride, and most of the tetrahydrofuran was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water; the organic layer was separated, washed with water, then with brine, and dried over sodium sulfate. The sample was concentrated and then purified by preparative thin layer chromatography (petroleum ether:ethyl acetate, 4:1) to provide pure product 31a as a white solid (995 mg, 88% yield). 1H-NMR (CDCl3, 400 MHz): δ 7.71 (d, J=8.4 Hz, 2H), 7.58 (d, J=6.8 Hz, 1H), 7.31 (d, J=8.4 Hz, 2H), 7.26 (d, J=6.8 Hz, 1H), 2.73 (q, J=8 Hz, 2H), 1.27 (t, J=8 Hz, 2H).

Workup

customthe reaction was quenched with saturated ammonium chloride
custommost of the tetrahydrofuran was evaporated under reduced pressure
customThe residue was partitioned between ethyl acetate and water
customthe organic layer was separated
washwashed with water
dry with materialwith brine, and dried over sodium sulfate
concentrationThe sample was concentrated
custompurified by preparative thin layer chromatography (petroleum ether:ethyl acetate, 4:1)

Sources & evidence

ORD record: ord-9991585795684ca09d1be204062cedcf
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09061060B2

Reaction notes

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