3-Fluoro-o-xylene

clear colorless liquid

General procedure: Trifluoroborate (0.50 mmol, 1.0 equiv), LiOH·HEXAMPLE 5 General procedure: Trifluoroborate (0.50 mmol, 1.0 equiv), LiOH·HA solution of 1-fluoro-2, 3-dimethylbenzene (30 g, 0.242 mol) and Bz2O2 (3 g, 0.012 mol) in CCI4 (400 mL) was heated to 600C. NBS (88 g, 0.494 mol) was added portionwise. After the addition, the reaction mixture was heated to 9O0C for 16 h and cooled to room temperature, filtered. The filtrate was concentrated and the residue was purified by column chromatography (eluting with petroleum ether) on silica gel to give pale yellow oil (65 g, 95percent).A mixture of [0527] Preparation of Compound 2 (Scheme 16): To a suspension of 1- fluoro-2, 3-dimethylbenzene (100 g, 0.81 mmol) in carbon tetrachloride(1.5 L) were added N-bromosuccinimide (288 g, 1.62 mmol), benzoyl peroxide (10 g). Themixture was heated to 70°C. After stirring for 15 h, the mixture was cooled to rt, poured into water (1 L) and extracted with DCM (3xlL). The combined organic layers were purified by flash column chromatography with petroleum ether to give the product 2 (161 g, 70percent) as white solid.TLC: PE/EA = 10/1; Rf (Compound 1) = 1; Rf (Compound 2) = 0.8To a solution of EXAMPLE 263; l, 2-Bis(bromomethvD- 3-fluorobenzene (263):A magnetically stirred mixture of 3-fluoro-o/t/zo-xylene (5.05g, 40.67 mmol), N- bromosuccinimide (15.23g, 85.56 mmol), AIBN (78mg) and CCl4 (75mL) is heated at reflux temperature for 1.75h, then cooled to RT. The solids are removed by filtration and washed with CCl4. The combined filtrate and wash is concentrated in vacuo on a rotary evaporator to give crude dibromide 263 as a yellow liquid that is dissolved in heptane-0.5percent EtOAc, placed atop a column of silica gel (7.2cm x 18cm) prepared in heptane-0.5percent EtOAc and flash chromatographed taking 20OmL fractions eluting with heptane-0.5percent EtOAc. Product containing fractions are combined and concentrated in vacuo on a rotary evaporator to afford a colorless liquid. On standing crystals form in the liquid. The liquid is separated using a pipette. The process is repeated once more. The resulting liquid is pure 1, 2 bis(bromomethyl)-3- fluorobenzene. [J. E. Rice, A. Czech, N, Hussain, E. J. La Voie, J. Org. Chem., 53, 1775-1779 (1988) ; R. A. Aitken, P. K.g. Hodgson, M. J. Morrison, A. O. Oyewale, J. Chem. Soc. (Perkin 1), 402-415 (2002)]209 EXAMPLE 5 Diazotization of 2, 3-dimethylaniline in Et3N-3HF 2, 3-Dimethylaniline (2.3 g, 0.02 mol) was syringed into Et3N-3HF (30 cm3) at 0° C. The addition of sodium nitrite (2.0 g, 0.03 mol) caused the evolution of gas under the influence of ultrasound, which was significant during the first 25 minutes. The clear reaction mixture gradually turned yellow and progressively darkened with the formation of tar. The brown mixture was poured into water (150 cm3) and extracted with diethyl ether (180 cm3*2). The remaining tarry residue was transferred to a Soxhlet apparatus and extracted repeatedly with diethyl ether (30 cm3) over 24 hours. The ether extracts were dried over magnesium sulphate and fractional removal of diethyl ether afforded a brown oil. Distillation of the oil at 142-143° C. at; atmospheric pressure afforded General procedure: Lithium bis(trimethylsilyl)amide (66.8 mg, 0.4 mmol) and cesium fluoride (30.4 mg, 0.2 mmol) were placed in a microwave tube in a glove box. Add 0.4 mL of cyclopentyl methyl ether, Then 2-fluorotoluene (66 muL, 0.60 mmol) and benzonitrile (20 muL, 0.20 mmol) were added separately using a micro syringe. which was taken out from the glove box and refluxed at 110 C for 12 hours. After cooling to room temperature, the reaction was capped and three drops of water were added to quench the reaction. The solvent was removed under reduced pressure and the crude product was purified by column chromatography ( petroleum ether: ethyl acetate = 20:1) to give 2-phenylindole (34.7 mg) , 90% yield).

Molecular Weight:124.15
XLogP3:3.1
Hydrogen Bond Acceptor Count:1
Exact Mass:124.068828449
Monoisotopic Mass:124.068828449
Heavy Atom Count:9
Complexity:90.6
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes