5-Bromo-2-nitrobenzaldehyde → 1-(5-Bromo-2-nitrophenyl)ethan-1-ol

HRID 2423517Notes

Reaction equation

[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:12]=1)[CH:10]=[O:11]>O1CCCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([N+:13]([O-:15])=[O:14])=[C:9]([CH:10]([OH:11])[CH3:1])[CH:12]=1

Participants

Conditions

Temperature: -78 °C

Procedure

Methyl magnesium bromide (7.97 mL of 3.0 M in tetrahydrofuran, 23.91 mmol) was added dropwise to 5-bromo-2-nitro-benzaldehyde (5.00 g, 21.73 mmol) in tetrahydrofuran (72 mL) at −78° C. After the addition was complete, the reaction was stirred for 15 min at −78° C. Then, the mixture was quenched with water and diethyl ether was added. The reaction was allowed to warm to room temperature and 10% citric acid solution was added. The layers were separated and the organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:7 ethyl acetate:hexanes to give 1.68 g (31%) of 1-(5-bromo-2-nitrophenyl)-ethanol as a solid. 1H NMR (400 MHz, d6-DMSO): δ 7.95 (d, J=2 Hz, 1H), 7.87 (d, J=9 Hz, 1H), 7.71 (dd, J=9, 2 Hz, 1H), 5.64 (d, J=4 Hz, 1H), 5.16-5.09 (m, 1H), 1.36 (d, J=6 Hz, 3H).

Workup

additionAfter the addition
customThen, the mixture was quenched with water and diethyl ether
additionwas added
temperatureto warm to room temperature
addition10% citric acid solution was added
customThe layers were separated
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with 1:7 ethyl acetate

Sources & evidence

ORD record: ord-bb75c65694564e98b46215129f97b914
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07960552B2

Reaction notes

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