Benzene, 1,3-bis(trifluoromethyl)- → 3-Bromo-4-(trifluoromethoxy)benzaldehyde
Reaction equation
FC(F)(F)C1C=CC=C(C(F)(F)F)C=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][C:26]([F:29])([F:28])[F:27])[C:19](Cl)=[O:20].[H][H]>O>[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[O:25][C:26]([F:27])([F:28])[F:29])[CH:19]=[O:20]Participants
5
Conditions
- Temperature
- 105 °C
Procedure
0.5 g of 5% palladium on barium sulfate (recovered from Example 1) and 48 g of 3-bromo-4-trifluoromethoxybenzoyl chloride were placed in a reaction vessel at room temperature with exclusion of water. A gentle stream of hydrogen gas was then introduced at atmospheric pressure. The mixture was subsequently heated to 100-110° C. and hydrogen gas was introduced continuously at atmospheric pressure. After liberation of acidic offgases had ceased (11 hours), the mixture was cooled to room temperature, the catalyst was removed by filtration and the filtrate was distilled at 25 mbar. At a boiling point of 112° C., 3-bromo-4-trifluoromethoxybenzaldehyde was obtained in a yield of 31.3 g. This corresponds to a yield of 74% of theory.
Workup
- custom(11 hours)
- temperaturethe mixture was cooled to room temperature
- customthe catalyst was removed by filtration
- distillationthe filtrate was distilled at 25 mbar
Sources & evidence
- ORD record
- ord-12eb12c1259e4a398547ade1cb6479d5
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06596906B2
Reaction notes
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