926293-55-2|6-Bromo-2-methylnicotinaldehyde| Ambeed

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CAS No. :	926293-55-2
Formula :	C₇H₆BrNO
M.W :	200.03
SMILES Code :	O=CC1=C(C)N=C(Br)C=C1
MDL No. :	MFCD13188654
InChI Key :	CUTAVXXGKKXAHQ-UHFFFAOYSA-N
Pubchem ID :	59596231

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: With n-butyllithium In hexanes; diethyl ether at -78℃; for 1 h; Stage #2: at -78 - 20℃; for 2 h;	Under N₂, to a solution of 2,5-dibromo-6-methylpyridine (35.5 g, 141.1 mmol) in anhydrous Et₂O (600 mL), cooled to -78 ⁰C, was added BuLi (2.5 M in hexanes, 64.8 mL, 162 mmol) slowly, forming a yellow suspension. After addition the mixture was stirred at that temperature for 1 h, and then anhydrous DMF (18.3 g, 250 mmol) was added. After the mixture was stirred at -78 ⁰C for 1 h, it was brought to room temperature and stirred for an additional 1 h. Aqueous HCl (0.5 N, 300 mL) was added and the organic layer was collected. The aqueous layer was extracted with EtOAc (3 x 150 mL). The combined extracts were dried (Na₂SO₄), filtered and the solvent was removed. The residue was purified by flash chromatography on silica gel (EtOAc/hexanes, 1 :3 in v/v) followed by recrystallization form CH₂Cl₂/hexanes, affording a pale yellow solid (21.5 g, 76percent). ¹H NMR (CDCl₃) δ 2.87 (s, 3H), 7.51 (d, IH, J= 8.1 Hz), 7.93 (d, IH, J= 8.1 Hz), 10.30 (s, IH).
51%	Stage #1: With n-butyllithium In diethyl ether; hexane at -78℃; for 1 h; Stage #2: at 20℃; for 1 h;	Add to the reaction flask3,6-dibromo-2-methylpyridine (1.0 g, 3.9 mmol)And anhydrous ether (10 mL) were cooled to -78°C,N-BuLi (1.6 M in hexanes, 2.4 mL, 3.9 mmol) was added dropwise,After stirring for 1 hour, anhydrous DMF (307 mg, 4.2 mmol) was added,The reaction was stirred at room temperature for 1 hour. Saturated ammonium chloride solution (10 mL) was added,Ethyl acetate (20 mL x 3). Combine organic phase,Saturated sodium chloride solution (20mL), dried over anhydrous sodium sulfate, suction filtration,Concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate / petroleum ether = 1: 10)The resulting residue was purified to give the title compound (0.4 g, white solid) in 51percent yield.
42.5%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere Stage #2: at -78 - 25℃; for 1 h; Inert atmosphere	To a solution of 3,6-dibromo-2-methylpyridine (60 g, 239 mmol) in THF (600 mL) and was added -BuLi (100 mL, 251 mmol) at -78 °C. The mixture was then stirred for 1 h at -78 °C under N₂ atmosphere. DMF (20.4 mL, 263 mmol) was added dropwise to the mixture. The mixture was then stirred for 1 h at -78 °C under N₂ atmosphere. The reaction mixture was warmed to 25 °C and 1 M aq. HC1 solution (300 mL) was added. The reaction mixture was combined with five additional crade reaction mixtures (performed at scales of 30 g, 120 mmol and 4 x 50 g, 199 mmol of 3,6-dibromo-2-methylpyridine using the same reagent and solvent stoichiometry as above) and worked up together. The reaction mixture was extracted with EtOAc (800 mL x 4). The combined organic layers were washed with H₂0 (300 mL x 3), dried over Na₂S04, filtered, and concentrated to give 6-bromo-2-methylnicotinaldehyde (260 g, 492 mmol, 42.5percent combined yield) as a red oil. NMR (400 MHz, CHLOROFORM-d) δ 10.28 (s, 1H), 7.92 (d, .7=7.9 Hz, 1H), 7.64 (s, 1H), 2.88 - 2.83 (m, 3H). LCMS [M+H]⁺ = 200.1, 202.1.

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CAS No.: 926293-55-2

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CAS No.: 926293-55-2

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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
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