4-Bromo-1-indanone

Orange-brown crystalline powder

General procedure: Trifluoromethane sulfonic acid (3 eq.) was gently added to a cooled (0 °C) solution of a 3-Phenylpropionic acid (0.5 mmol) in dry CHTo a solution of 3-(2-bromophenyl)propanoic acid (1.20 g, 5.24 mmol, CAS 15115-58-9) in a mixture of solvent dichloromethane (20 mL) and dimethylformamide (3.83 mg, 52.4 umol) was added oxalyl chloride (1.33 g, 10.4 mmol) and the reaction mixture was stirred at 20 °C for 1 hr. On completion, the mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (20 mL) and cooled to 0 °C. Then aluminum trichloride (838 mg, 6.29 mmol) was added at 0 °C and the reaction mixture was stirred at 0 °C for 1 hr. On completion, the reaction mixture was poured into 100 mL cool water and extracted with DCM (3 X 50 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (1.10 g, 95percent yield) as a light yellow solid.4-Bromo-2, 3-dihydro-1H-inden-1-one (2) [00161] 4-Bromo-2, 3-dihydro-lH-inden-l-one (b): 3-(2-Bromophenyl)propanoic acid (a) (550 g, 2.4 mol, 1 equiv) was dissolved in 1 , 2-dichloroethane (5.5 L). Thionyl chloride (437.8 niL, 6 mol, 2.5 equiv) was added to the solution and the mixture was refluxed for 24 hours. The reaction was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in methylene chloride (1 L) and added dropwise to a mechanically stirred suspension of anhydrous aluminum chloride (526.9 g, 3.96 mol, 1.65 equiv) in dichloromethane (1 L) while keeping the reaction temperature below 27°C. The reaction was stirred at room temperature for three hours before being quenched into a five gallon bucket which was half-full of ice. The resulting mixture was extracted with dichloromethane (3 x 3 L). The combined organic layers were washed sequentially with saturated brine (2 L) and saturated sodium bicarbonate (2 L). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting solid was dried overnight in a vacuum oven at 30°C to give compound b (435 g, 86percent yield) as an off-white solid.Example NINETEEN-1 (Compound 149) [4-BROMO-INDAN-1-ONE] was obtained by the following procedure: A solution of [3- (2-BROMO-PHENYL)-PROPIONIC] acid (commercially available from Oakwood Products) (15.0 g, 65.5 mmol) in [CHUCK] at [0 °C] was reacted with oxalyl chloride (7.2 mL, 1.5 eq) followed by 2-3 drops of DMF. The mixture was stirred until no more gas evolution was observed. As the mixture was concentrated and the residue was dissolved in [CH2C12, ] cooled to [0 °C, ] and treated with [AIDS] (9.6 g, 1.1 eq). After 1 h the mixture was quenched with water and the layers were separated. The aqueous layer was extracted with Et2O (3 x 150 [ML)] and the combined organic extracts were washed with H20 (3 x 100 mL), saturated NaHCO3 (3 x 100 mL), brine (1 x 100 [ML), ] dried over MgS04 and concentrated. [4-BROMOINDAN-L-ONE, ] 10.5 g (76percent) was obtained by chromatography using 10 percent EtOAc: hexane as eluant. Use of 4-bromo- [INDAN-1-ONE] in Method NINETEEN produced [4- (4-BROMO-INDAN-2-YL)-1, ] 3-dihydro- imidazole-2-thione (Compound 149). 1H NMR (300 MHz, DMSO-d6) 8 12.0 (s, 1H), 11.7 (s, 1H), 7.34 (d, J= 7.8 Hz, 1H), 7.22 (d, [J=] 7.5 Hz, 1H), 7.09 (t, J= 7.5 Hz, [1H), ] 6.63 (s, [1H), ] 3.50-3. 40 (m, [1H), ] 3.30-3. 12 (m, 2H), 3.06-2. 85 (m, 2H).3-(2-Bromophenyl)propanoic acid (1) (550 g, 2.4 mol, 1 equiv) was dissolved in 1, 2-dichloroethane (5.5 L). Thionyl chloride (437.8 mL, 6 mol, 2.5 equiv) was added to the solution and the mixture was refluxed for 24 hours. The reaction was cooled to room temperature and concentrated under reduced pressure. The residue was dissolved in methylene chloride (1 L) and added dropwise to a mechanically stirred suspension of anhydrous aluminum chloride (526.9 g, 3.96 mol, 1.65 equiv) in dichloromethane (1 L) while keeping the reaction temperature below 27° C. The reaction was stirred at room temperature for three hours before being quenched into a five gallon bucket which was half-full of ice. The resulting mixture was extracted with dichloromethane (3×3 L). The combined organic layers were washed sequentially with saturated brine (2 L) and saturated sodium bicarbonate (2 L). The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting solid was dried overnight in a vacuum oven at 30° C. to give compound 2 (435 g, 86percent yield) as an off-white solid.

Molecular Weight:211.05
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Exact Mass:209.96803
Monoisotopic Mass:209.96803
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes