1654735-54-2 → 1-Bromo-4-fluoro-2-isopropylbenzene

HRID 632661Notes

Reaction equation

HRID 632661 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

HCID 903591701654735-54-2

Product 1

HCID 207544981-Bromo-4-fluoro-2-isopropylbenzene

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 6344DichloromethaneSolvent

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

  1. filtrationwas filtered through Celite™
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dc2f79f6c374601ae46caeb4dcc3d61
Source dataset
uspto-grants-2016_04
Patent number
US09321746B2

Reaction notes

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