61563-28-8|2-Chloro-3-methylbenzaldehyde| Ambeed

CAS No. :	61563-28-8
Formula :	C₈H₇ClO
M.W :	154.59
SMILES Code :	O=CC1=CC=CC(C)=C1Cl
MDL No. :	MFCD11845907
InChI Key :	LGOLMLQWRYFRHP-UHFFFAOYSA-N
Pubchem ID :	14492779

Safety of [ 61563-28-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 61563-28-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 61563-28-8 ]

[ 61563-28-8 ] Synthesis Path-Downstream 1~51

1
[ 134271-45-7 ]
[ 61563-28-8 ]

References: [1]Journal of Organometallic Chemistry,1991,vol. 401,p. 261 - 272.

2
[ 565-62-8 ]
[ 68-12-2 ]
[ 61563-28-8 ]
[ 102626-21-1 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1989,vol. 28,p. 494 - 495.

3
[ 6781-98-2 ]
[ 61563-28-8 ]

References: [1]Journal of Organometallic Chemistry,1991,vol. 401,p. 261 - 272.

4
[ 61563-27-7 ]
[ 61563-28-8 ]

Yield	Reaction Conditions	Operation in experiment
91.4%		A solution of DCM (30 ML) was cooled TO-78C and oxalyl chloride (1.34 ml, 15. 2MMOL, 1.2eq) was added under nitrogen followed by dropwise addition of DMSO (2.2 ml, 31.7mmol, 2. 5EQ) in DCM (10ml). After stirring for 15 min a solution of 2- chloro-3-methylbenzylalcohol (2g, 12.7mmol, leq) in DCM (12 ml) was added dropwise. After a further 30 min triethylamine (9.03 ml, 63. 5MMOL, 5EQ) was added in one portion and the mixture warmed to room temperature over 1 hour. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate (50 ml) and the aqueous layer extracted with DCM (2 x 50 ml). The combined organic extracts were dried (MGS04) and the solvent removed in vacuo to give 2-chloro-3-methylbenzaldehyde (1.8g, 91.4%) as a yellow oil; 1H NMR (300 MHz, CDC13) 8= 10. 53 (1H, s, CHO), 7.81- 7.74 (1H, m, ArH), 7.53-7. 46 (1H, m, ArH), 7.34-7. 23 (1H, m, ArH) and 2.46 (3H, s).
	With manganese(IV) oxide; In dichloromethane; at 25℃; for 12h;Inert atmosphere;	To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After the addition, the reaction mixture was stirred at 25 C for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ether:ethyl acetate = 20:1) to give the title compound.1H NMR (400MHz, DMSO-d6) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J = 8.2 Hz, 2H), 7.42 (t, J = 7.5 Hz, 1H), 2.39 (s, 3H)
	With manganese(IV) oxide; In dichloromethane; at 25℃; for 12h;Inert atmosphere;	Step 2 - 2-Chloro-3-methylbenzaldehyde (0337) [00250] To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After the addition, the reaction mixture was stirred at 25 C for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ether:ethyl acetate = 20:1) to give the title compound.1H NMR (400MHz, DMSO-d6) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J=8.2 Hz, 2H), 7.42 (t, J=7.5 Hz, 1H), 2.39 (s, 3H).

With manganese(IV) oxide; In dichloromethane; at 20℃; for 12h;Inert atmosphere;

To a solution of (2-chloro-3-methyl-phenyl)methanol (26.2 g, 167 mmol) in dichloromethane (350 mL) was added manganese dioxide (116 g, 1.34 mol) under nitrogen. After, the reaction mixture was stirred at rt for 12 hrs. The solid was filtered, and the filtrate was concentrated under vacuum. The residue was purified by column chromatography (eluted with petroleum ethenethyl acetate = 20: 1) to give the title compound. NMR (400MHz, DMSO-d5) delta = 10.42 - 10.34 (m, 1H), 7.68 (t, J = 8.2 Hz, 2H), 7.42 (t, J= 7.5 Hz, 1H), 2.39 (s, 3H).

References: [1]Patent: WO2004/52858,2004,A2 .Location in patent: Page 133.
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 892 - 913.
[3]Patent: WO2017/156177,2017,A1 .Location in patent: Paragraph 00276.
[4]Patent: WO2017/156181,2017,A1 .Location in patent: Paragraph 00250.
[5]Patent: WO2017/156165,2017,A1 .Location in patent: Paragraph 00316; 00319; 00320.

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 2-Chloro-3-methylbenzoic acid was reduced by treating with diborane in tetrahydrofuran and the resulting 2-chloro-3-methylbenzyl alcohol was oxidized with activated magnesium dioxide in methylene chloride to give 2-chloro-3-methylbenzaldehyde.

6
[ 1816-92-8 ]
[ 61563-28-8 ]
methyl 2-azido-3-(2-chloro-3-methylphenyl)acrylate [ No CAS ]