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ChemicalBook CAS DataBase List 4-BROMO-3-TRIFLUOROMETHYL-BENZALDEHYDE
34328-47-7

4-BROMO-3-TRIFLUOROMETHYL-BENZALDEHYDE synthesis

4synthesis methods
(4-BROMO-3-TRIFLUOROMETHYL-PHENYL)-METHANOL

957207-09-9

4-BROMO-3-TRIFLUOROMETHYL-BENZALDEHYDE

34328-47-7

Example 12 Preparation of 4-bromo-3-(trifluoromethyl)benzaldehyde (C70): to a solution of (4-bromo-3-(trifluoromethyl)phenyl)methanol (C72) (12.0 g, 47.1 mmol) in dichloromethane (100 mL) was added manganese dioxide (25.6 g, 294 mmol). The reaction mixture was stirred at room temperature for 12 hours before being filtered through a Celite pad to remove solid impurities. The filtrate was concentrated under reduced pressure to afford 3-trifluoromethyl-4-bromobenzaldehyde as a light yellow solid (10.0 g, 82% yield). The product was characterized by the following data: 1H NMR (300 MHz, CDCl3) δ10.05 (s, 1H), 8.19 (s, 1H), 7.94-7.88 (m, 2H); IR (thin film) 1704, 1123 cm-1; EIMS m/z 219 ([M]+).

-

Yield: 82%

Reaction Conditions:

with manganese(IV) oxide in dichloromethane for 12 h;

Steps:

12 Example 12
Example 12
Preparation of 4-bromo-3-(trifluoromethyl)benzaldehyde (C70)
To a solution of (4-bromo-3-(trifluoromethyl)phenyl)methanol (C72) (12.0 g, 47.1 mmol) in dichloromethane (100 mL) was added manganese dioxide (25.6 g, 294 mmol).
After stirring for 12 hours, the mixture was filtered through Celite and the filtrate was concentrated in vacuo to afford the title compound as a pale yellow solid (10.0 g, 82%): 1H NMR (300 MHz, CDCl3) δ 10.05 (s, 1H), 8.19 (s, 1H), 7.94-7.88 (m, 2H); IR (thin film) 1704, 1123 cm-1; EIMS m/z 219 ([M]+).

References:

Dow AgroSciences LLC;LePlae, JR., Paul R.;Barton, Thomas;Gao, Xin;Hunter, James E.;Lo, William C.;Boruwa, Joshodeep;Tangirala, Raghuram;Watson, Gerald B.;Herbert, John;Demeter, David A.;Joshi, Hemant US2018/279612, 2018, A1 Location in patent:Paragraph 0382-0383

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