[ CAS No. 54335-33-0 ]

Name: Methyl 2,4-dibromobenzoate
Brand: Ambeed
SKU: A127370
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COA GC NMR CNMR HPLC/UPLC LC-MS SDS

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SDS

Product Details of [ 54335-33-0 ]

CAS No. :	54335-33-0	MDL No. :	MFCD09954350
Formula :	C₈H₆Br₂O₂	Boiling Point :	308°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	293.94	Pubchem ID :	22572357
Synonyms :

Computed Properties of [ 54335-33-0 ]

TPSA :Topological Polar Surface Area	26.3	H-Bond Acceptor Count :	2
XLogP3 :	-	H-Bond Donor Count :	0
SP3 :	0.13	Rotatable Bond Count :	2

Safety of [ 54335-33-0 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 54335-33-0 ]

Upstream synthesis route of [ 54335-33-0 ]
Downstream synthetic route of [ 54335-33-0 ]

[ 54335-33-0 ] Synthesis Path-Upstream 1~4

1
[ 67-56-1 ]
[ 611-00-7 ]
[ 54335-33-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 0℃; for 3.00 h; Reflux	At 0 °C, thionyl chloride (3.57 g, 30 mmol) was added dropwise into a solution of 2,4-dibromobenzoicacid (5.60 g, 20 mmol) in methanol (100 mL) slowly. The ice-salt bath used was removed after that dropping and then the reaction mixture was heated to reflux for 3 hours. TLC and LCMS indicated that starting materials reacted completely. The solvent and excess thionyl chloride were removed by rotary evaporation to give a crude product. Then the crude product was dissolved in dichloromethane (100 mL), washed successively with saturated sodium bicarbonate solution (100 mLx2) and saturated brine (100 mL), dried with anhydrous sodium sulfate and filtered. A yellow solid product (5.92 g, 100percent yield) was obtained by rotary evaporation. The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 292.8/294.7/269.9 [M+H]⁺.
96%	at 0℃; Reflux	General procedure: The corresponding acid (5 mmol) was dissolved in CH3OH (20 mL), and then H2SO4 (8 equiv) was added at 0 °C, the reaction mixture was then refluxed for 24–48 h. After cooling, the solvent was evaporated. To the resulting mixture was slowly added a solution of 10percent Na2CO3 (200 mL), and then the aqueous solution was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography to obtain compound 3 or compound 4a and 4b.
213.6 g	Reflux	Step 1: To a 2 L round-bottom flask, 2,4-dibromobenzoicacid (250 g, 0.90 mol) in MeOH (2 L) and concentrated H₂SO₄ (18.4 g, 0.19 mol) were added. The mixture was refluxed overnight before cooled to room temperature. The resulting precipitate was then filtered, washed with cold methanol and dried under vacuum. It yielded 213.6 g methyl 2,4-dibromobenzoate as a yellow solid. To a 2 L round-bottom flask was added 2,4-dibromobenzoate (200.7 g, 0.69 mol) in 1 L dry DMF. CuCN (123.8 g, 1.38 mol) and NaI (22.8 g, 0.15 mol) were introduced next. The mixture was stirred overnight at 160 °C under nitrogen atmosphere. After the reaction was complete, it was extracted with ethyl acetate (500 mL × 3),washed with water (500 mL) and purified over silica gel (PE/EtOAc = 5/1) to give 93.5 g methyl 2,4-dicyanobenzoate as a brown solid (yield: 72.8 percent).

Reference： [1] Patent: EP3048103, 2016, A1. Location in patent: Paragraph 0077; 0078
[2] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2490 - 2494
[3] Chemistry - A European Journal, 2010, vol. 16, # 6, p. 1780 - 1784
[4] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6655 - 6657

2
[ 611-00-7 ]
[ 54335-33-0 ]

Reference： [1] Journal of the Chemical Society, 1895, vol. 67, p. 602

3
[ 78222-69-2 ]
[ 54335-33-0 ]

Reference： [1] Journal of the Chemical Society, 1895, vol. 67, p. 602

4
[ 67-56-1 ]
[ 59615-16-6 ]
[ 54335-33-0 ]

Reference： [1] Journal of the Chemical Society, 1895, vol. 67, p. 602

[ 54335-33-0 ] Synthesis Path-Downstream 1~10

1
[ 67-56-1 ]
[ 59615-16-6 ]
[ 54335-33-0 ]

Reference： [1]Journal of the Chemical Society,1895,vol. 67,p. 602

2
[ 54335-33-0 ]
5-(aminomethyl)isoindolin-1-one [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 6655 - 6657

3
[ 54335-33-0 ]
5-(aminomethyl)isoindolin-1-one hydrochloride [ No CAS ]

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 6655 - 6657

4
[ 54335-33-0 ]
copper(l) cyanide [ No CAS ]
[ 58331-99-0 ]

Yield	Reaction Conditions	Operation in experiment
72.8%	With sodium iodide; In N,N-dimethyl-formamide; at 160℃;Inert atmosphere;	Step 1: To a 2 L round-bottom flask, 2,4-dibromobenzoicacid (250 g, 0.90 mol) in MeOH (2 L) and concentrated H2SO4 (18.4 g, 0.19 mol) were added. The mixture was refluxed overnight before cooled to room temperature. The resulting precipitate was then filtered, washed with cold methanol and dried under vacuum. It yielded 213.6 g <strong>[54335-33-0]methyl 2,4-dibromobenzoate</strong> as a yellow solid. To a 2 L round-bottom flask was added 2,4-dibromobenzoate (200.7 g, 0.69 mol) in 1 L dry DMF. CuCN (123.8 g, 1.38 mol) and NaI (22.8 g, 0.15 mol) were introduced next. The mixture was stirred overnight at 160 °C under nitrogen atmosphere. After the reaction was complete, it was extracted with ethyl acetate (500 mL × 3),washed with water (500 mL) and purified over silica gel (PE/EtOAc = 5/1) to give 93.5 g methyl 2,4-dicyanobenzoate as a brown solid (yield: 72.8 percent).

Reference： [1]Asian Journal of Chemistry,2014,vol. 26,p. 6655 - 6657

5
[ 54335-33-0 ]
[ 62-53-3 ]
methyl 2,4-dianilinobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃;Inert atmosphere;	General procedure: To a solution of benzoic acid methyl ester (3, 4a,b) (500 mg), the respective arylamine compounds (2.4 equiv for 3, 1.2 equiv for 4a,b), Cs2CO3 (2.8 equiv for 3, 1.4 equiv for 4a,b), BINAP (0.08 equiv) in 1,4-dioxane (5 mL) was added Pd(OAc)2 (5 mol percent) under nitrogen. And the reaction mixture was stirred at 100 °C for 10?24 h. The reaction mixture was cooled to room temperature, and then H2O was added. The mixture was extracted with ethyl acetate, and then the organic layers were combined, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography.