62358-81-0|1-(Bromomethyl)-3-chloro-5-methylbenzene| Ambeed

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CAS No. :	62358-81-0
Formula :	C₈H₈BrCl
M.W :	219.51
SMILES Code :	CC1=CC(Cl)=CC(CBr)=C1
MDL No. :	MFCD18393677

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; potassium tert-butylate; silver nitrate; dibenzoyl peroxide; In tetrachloromethane; water;	3-Chloro-5-methylbenzoic acid A well stirred mixture of N-bromosuccinimide (32.5 g), 5-chloro-m-xylene (25.6 g) and carbon tetrachloride (500 ml) is refluxed for 8 hours. The solution is well illuminated and every 2 hours small quantities of benzoyl peroxide are added. The cooled mixture is filtered and the solvent evaporated to give an oil consisting of a mixture of 3-chloro-5-methylbenzyl bromide and 5-chloro-m-xylene in a ratio of about 2:1 (34.5 g). The above mixture is added to a stirred mixture of potassium tert-butoxide (14 g), 2-nitropropane (11 g) and dimethylsulphoxide (100 ml) and the mixture is stirred overnight at room temperature. Water (500 ml) is added and the separated oil extracted with ether. Evaporation of the dried ether solution yields an oil consisting of a mixture of <strong>[103426-20-6]3-chloro-5-methyl-benzaldehyde</strong> and 5-chloro-m-xylene (approximately 1:1) (18.5 g). The above mixture is slowly added over a 15 minute period to a stirred suspension of moist silver oxide [prepared from silver nitrate (24 g) and an aqueous solution of sodium hydroxide (5.7 g)] in a solution of sodium hydroxide (5.7 g) in water (50 ml). The stirred mixture is refluxed for 30 minutes, cooled, filtered and the filtrate extracted with ether. Acidification of the aqueous layer with 2N HCl yields a precipitate which is filtered and recrystallized from aqueous methanol to yield 3-chloro-5-methylbenzoic acid, 174-175 C. (9.4 g).
	With hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; potassium tert-butylate; silver nitrate; dibenzoyl peroxide; In tetrachloromethane; water;	3-Chloro-5-methylbenzoic acid A well stirred mixture of N-bromosuccinimide (32.5 g), 5-chloro-m-xylene (25.6 g) and carbon tetrachloride (500 ml) is reflexed for 8 hours. The solution is well illuminated and every 2 hours small quantities of benzoyl peroxide are added. The cooled mixture is filtered and the solvent evaporated to give an oil consisting of a mixture of 3-chloro-5-methyl-benzyl bromide and 5-chloro-m-xylene in a ratio of about 2:1 (34.5 g). The above mixture is added to a stirred mixture of potassium tert-butoxide (14 g), 2-nitropropane (11 g) and dimethylsulphoxide (100 ml) and the mixture is stirred overnight at room temperature. Water (500 ml) is added and the separated oil extracted with ether. Evaporation of the dried ether solution yields an oil consisting of a mixture of <strong>[103426-20-6]3-chloro-5-methyl-benzaldehyde</strong> and 5-chloro-m-xylene (approximately 1:1) (18.5 g). The above mixture is slowly added over a 15 minute period to a stirred suspension of moist silver oxide [prepared from silver nitrate (24 g) and an aqueous solution of sodium hydroxide (5.7 g)] in a solution of sodium hydroxide (5.7 g) in water (50 ml). The stirred mixture is refluxed for 30 minutes, cooled, filtered and the filtrate extracted with ether. Acidification of the aqueous layer with 2N HCl yields a precipitate which is filtered and recrystallized from aqueous methanol to yield 3-chloro-5-methylbenzoic acid, 174-5 C. (9.4 g).

Yield	Reaction Conditions	Operation in experiment
42%	With 2-nitropropane; sodium hydride; In ethanol; for 3.0h;	[00327] To a solution of sodium metal ( 52 mg, 2.3mmol) in ethanol was added 2- nitropropane (0.23g, 2.4 mmole) followed by the addition of 3-chloro-5-methybenzylbromide (0.5g, 2.3 mmol). The reaction was allowed to stir for 3 hours and the precipitate formed was filtered off. The filtrate was concentrated under reduced pressure, redissolved in diethylether and washed with IN sodium hydroxide (twice), water, and dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography using 10% dichloromethane and 90% petroleum ether, to give 0.15g of 3-chloro-5-methylbenzaldehyde (42%). 1H-NMR (CDCl3): 2.46 (s, 3H) 7.43(s, IH) 7.56 (s, IH) 7.68(s, IH), 9.92 (s, IH).
	With 2-nitropropane; sodium ethanolate; In ethanol; for 3.0h;	[0363] To a solution of sodium metal ( 52 mg, 2.3mmol) in ethanol was added 2- nitropropane (0.23g, 2.4 mmole) followed by the addition of 3-chloro-5-methybenzylbromide (0.5g, 2.3 mmol). The reaction was allowed to stir for 3 hours and the precipitate formed was filtered off. The filtrate was concentrated under reduced pressure, redissolved in diethylether and washed with IN sodium hydroxide (twice), water, and dried over sodium sulfate, filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography using 10% dichloromethane and 90% petroleum ether, to give 0.15g of 3-chloro-5-methylbenzaldehyde. 1H-NMR (CDCl3): 2.46 (s, 3H) 7.43(s, IH) 7.56 (s, lH) 7.68(s, IH), 9.92 (s, IH).

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CAS No.: 62358-81-0

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CAS No.: 62358-81-0

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[ 62358-81-0 ] Synthesis Path-Downstream 1~2

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
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