Heptane → Methyl 2-bromo-2-(4-nitrophenyl)acetate
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1.[Br:15]N1C(=O)CCC1=O.CCCCCCC>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:14])[CH:4]([Br:15])[C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1Participants
Conditions
- Temperature
- 74 °C
Procedure
(4-Nitro-phenyl)-acetic acid methyl ester (500 mg, 2.56 mmol) was dissolved in carbon tetrachloride (6.00 mL) and N-bromosuccinimide (502 mg, 2.82 mmol) was added followed by 2,2′-azo-bis-isobutyronitrile (12.6 mg, 0.0768 mmol). The reaction was heated at 74° C. overnight. The reaction was then cooled to room temperature and poured into heptane (25 mL). The resulting suspension was filtered and the filter cake washed with heptane (15 mL). The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography using a gradient of 0-25% EtOAc/hex as the eluting solvent to obtain bromo-(4-nitro-phenyl)-acetic acid methyl ester as a clear-colorless oil (547 mg, 78%). LCMS (m/e) 274 (M+H); 1H-NMR (CDCl3, 400 MHz) δ 8.23 (d, 2H, J=8.6 Hz), 7.73 (d, 2H, J=8.6 Hz), 5.40 (s, 1H), 3.82 (s, 3H).
Workup
- temperatureThe reaction was then cooled to room temperature
- filtrationThe resulting suspension was filtered
- washthe filter cake washed with heptane (15 mL)
- concentrationThe filtrate was concentrated under reduced pressure
- customthe resulting residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-660e88a41c42472593cb089675a4ca29
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08471005B2
Reaction notes
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