1654735-54-2 → 1-Bromo-4-fluoro-2-isopropylbenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]([CH3:11])=[CH2:10]>C(Cl)Cl.[Rh]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH:9]([CH3:11])[CH3:10]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 1-bromo-4-fluoro-2-(prop-1-en-2-yl)benzene (200 mg, 0.930 mmol) in DCM (5 mL) was added 5% Rhodium on Alumina (30 mg, 0.015 mmol). The resulting mixture was stirred under hydrogen atmosphere (50 psi) for 18 h after which time the reaction was filtered through Celite™ and concentrated in vacuo to afford 1-bromo-4-fluoro-2-isopropylbenzene. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.48 (dd, J=8.6, 5.7 Hz, 1H), 7.01 (dd. J=10.3, 3.1 Hz, 1H), 6.82-6.75 (m, 1H), 3.38-3.25 (m, 1H), 1.21 (d, J=6.9 Hz, 6H).
Workup
- filtrationwas filtered through Celite™
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8dc2f79f6c374601ae46caeb4dcc3d61
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321746B2
Reaction notes
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