N-bromobutanimide → 3-Bromo-6-fluoro-2-methyl-benzoic acid

HRID 577469Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:3]=1[C:4]([OH:6])=[O:5].C1C(=O)N([Br:19])C(=O)C1>OS(O)(=O)=O>[Br:19][C:8]1[C:7]([CH3:11])=[C:3]([C:2]([F:1])=[CH:10][CH:9]=1)[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 0 °C

Procedure

To a 0° C. solution of 2-fluoro-6-methyl-benzoic acid (1.48 g, 9.60 mmol) in conc. H2SO4 (40 mL) was added NBS (1.79 g, 10.1 mmol). The mixture was stirred at 0° C. for 3 hours. The reaction mixture was poured into ice water (200 mL), and extracted with ether (2×200 mL). The organic layers were combined, dried over sodium sulfate, and concentrated under vacuum to give the title compound (Compound QQ, 2.15 g, 96% yield) as a solid. 1H NMR (400 MHz, chloroform-d) δ 7.64 (dd, J=8.84, 5.31 Hz, 1H), 6.92 (t, J=8.84 Hz, 1H), 2.54 (s, 3H); MS 231.0 [M+H].

Workup

extractionextracted with ether (2×200 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-9c268ca009864a5b9aa8a0f4d14ccb0c
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040515B2

Reaction notes

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