Water → N-methyl-2-(2-bromomethylphenyl)-2-methoxyiminoacetamide

HRID 991416Notes

Reaction equation

[C:1]([Br:5])(Br)(Br)Br.[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1CO)=[N:10][O:11][CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:6][NH:7][C:8](=[O:21])[C:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:1][Br:5])=[N:10][O:11][CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Carbon tetrabromide (0.33 g) was added to a solution of N-methyl-2-(2-hydroxymethylphenyl)-2-methoxyiminoacetamide (0.11 g) and triphenylphosphine (0.26 g) in tetrahydrofuran (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1½ hours and then at room temperature for 1 hour. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The combined extracts were washed with brine and dried over magnesium sulphate. The solution was then concentrated under reduced pressure to leave a gum. Column chromatography (eluting with diethyl ether on silica gel) gave the N-methyl-2-(2-bromomethylphenyl)-2-methoxyimino-acetamide as a gum (80 mg, 57%). 1H NMR (CDCl3) δ2.95(d,3H), 4.0(s,3H), 4.35(s,2H), 6.8(brs,1H), 7.1-7.5(m,4H) ppm.

Workup

extractionextracted three times with ethyl acetate
washThe combined extracts were washed with brine
dry with materialdried over magnesium sulphate
concentrationThe solution was then concentrated under reduced pressure
customto leave a gum
washColumn chromatography (eluting with diethyl ether on silica gel)

Sources & evidence

ORD record: ord-5e4a6f1e925849f286927a5d7d934790
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06465457B1

Reaction notes

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