Sulfuric Acid → N-[2-(3-Bromophenyl)-1,1-dimethylethyl]-2-chloroacetamide

HRID 1866506Notes

Reaction equation

[Cl:1][CH2:2][C:3]#[N:4].[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([CH3:16])(O)[CH3:14])[CH:9]=[CH:10][CH:11]=1.S(=O)(=O)(O)[OH:18].C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C>[Br:5][C:6]1[CH:7]=[C:8]([CH2:12][C:13]([NH:4][C:3](=[O:18])[CH2:2][Cl:1])([CH3:14])[CH3:16])[CH:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Chloroacetonitrile (6.63 ml, 105 mmol) was added to a stirred solution of 1-(3-bromophenyl)-2-methylpropan-2-ol) (Preparation 29) (12.0 g, 52.0 mmol) in acetic acid (25 ml) at room temperature. The resulting solution was cooled to 0° C. and concentrated sulfuric acid (25 ml) was added keeping the temperature<10° C. The resulting solution was left to stir for 1 hour and then poured onto ice and basified by the addition of solid potassium carbonate. The product was extracted with ethyl acetate (2×500 ml), the organics combined and washed with water (50 ml), dried (sodium sulfate) and the solvent removed in vacuo to afford the title compound as an orange solid (16.08 g). 1H NMR (400 MHz, CDCl3) δ 7.39-7.32 (1H, d), 7.26 (1H, s), 7.1-7.13 (1H, t), 7.08-7.03 (1H, d), 6.17 (1H, bs), 3.94 (2H, s), 3.02 (2H, s), 1.37 (6H, s). CHN for C12H15BrClNO calc. (found): C, 47.32 (47.26); H, 4.96 (4.87); N, 4.60 (4.65). LRMS (electrospray) m/z 306 [M+H]+

Workup

customthe temperature<10° C
waitThe resulting solution was left
additionpoured onto ice
extractionThe product was extracted with ethyl acetate (2×500 ml)
washwashed with water (50 ml)
dry with materialdried (sodium sulfate)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-250ade9209d041deb6116fc723998a50
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07629358B2

Reaction notes

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