2-Bromo-5-chlorobenzaldehyde

General procedure: The benzyl alcohols substrates (1a–1p) (0.2mmol), FeClGeneral procedure: To 10 mL of a microwave tube was added benzyl alcohol (0.5 mmol, 61.2 mg) and triphenylmethanol (0.5 mmol, (0.015 mmol, 11 mg) was added, the reaction mixture was heated to 120 ° C with a microwave reactor, and the reaction was stirred for 60 minutes. After completion of the reaction, the reaction product was separated by flash column chromatography to obtain the desired product I, 92percent.Substitution of 37.0 mg of Ph3PAuNTf2 for 11 mg of Ph3PAuNTf2, In the same manner as in Example 1, The target compound I, Yield 96percent.2-bromo-5-chlorobenzyl alcohol was used in place of 2-bromo-5-fluorobenzyl alcohol, In the same manner as in Example 4, The target compound V, Yield 85percent.Step 2: 2-bromo-5-chlorobenzaldehyde; 2-bromo-5-chlorobenzaldehyde was prepared according to literature precedent (/. Am. Chem. Soc. 2002, 124 (7), 1354): a mixture of activated powdered 4A molecular sieves (800 mg/mmol substrate), N- methylmorpholine-N-oxide (2 eq) and 2-bromomethyl-5-chlorobenzaldehyde (1 eq) in MeCN (0.16 M) was stirred at 0 Concentrated sulfuric acid (mass fraction 98percent, 150mL) was added to the reactor to reduce the temperature.The temperature of the system is ≤ 10°C, the compound A liquid (3-chlorobenzaldehyde, 0.5 mol) is slowly added dropwise, and after addition, an appropriate amount of catalyst I2 (0.236-2.36 mmol, 30 mg in this example) is added.When 3-chlorobenzaldehyde and catalyst 12 were added, there was a clear exothermic phenomenon and the reaction temperature of the system was controlled to be ≤ 10°C; System temperature control ≤15°C, add in batches 5-10 timesNBS (N-bromosuccinimide, 0.5 mol); Insulation reaction for 2h, slowly rise to 25 °C, and stir the reaction for 1h, GC detection of raw materials 3_ chlorobenzaldehyde content ≤ 1 percent, The reaction solution was purified by post-treatment to obtain an acicular off-white solid compound (98 g, purity 98.0percent, yield 90.1 percent).(2-Bromo-5-chlorophenyl)methanediyl diacetate(1.5 g, 4.7 mmol) was refluxed in MeOH–H2O (15 mL, 1/1 V/V) containing H2SO4 (1.6 mL)for 30 min. The reaction mixture was then diluted with H2O (15 mL) and extracted withEtOAc (3×20 mL). The combined organic layers were washed with H2O (20 mL) and brine(20 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue and 1 Mhydrochloric acid (4.0 mL) were heated for 3 h in THF (15 mL) under reflux. The solvent wasremoved under reduced pressure. The residue was purified by column chromatography (SiO2, hexane/EtOAc = 95/5). Yield: 0.84 g, 83 percent.Example 72

Molecular Weight:219.46
XLogP3:2.7
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:217.91341
Monoisotopic Mass:217.91341
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes