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Chemistry
Organic Building Blocks
Aryls
Ethyl 4-bromo-3-(bromomethyl)benzoate
Chemistry
Organic Building Blocks
Aryls
Bromides Esters Benzyl bromides Benzene Compounds

[ CAS No. 347852-72-6 ]

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Quality Control of [ 347852-72-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 347852-72-6 ]

CAS No. :347852-72-6 MDL No. :MFCD16249633
Formula : C10H10Br2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :BMPAWOLCRAJVPC-UHFFFAOYSA-N
M.W :321.99 Pubchem ID :22574851
Synonyms :

Safety of [ 347852-72-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405 UN#:3261
Hazard Statements:H314-H290 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 347852-72-6 ]

* 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 [ 347852-72-6 ]

[ 347852-72-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 160313-69-9 ]
  • [ 347852-72-6 ]
YieldReaction ConditionsOperation in experiment
62% With N-Bromosuccinimide; dibenzoyl peroxide In Carbon tetrachloride Reflux; 3.A Step A. Ethyl 4-bromo-3-(bromomethyl)benzoate Step A. Ethyl 4-bromo-3-(bromomethyl)benzoate Ethyl 4-bromo-3-methylbenzoate (110 g, 450 mmol.) was treated with NBS according to the procedure of Example 5. Silica gel chromatography with hexanes/ethyl acetate as eluant provided ethyl 4-bromo-3-(bromomethyl)benzoate (91 g, 62%) as a white solid. General Method 1: Benzylic Bromination Using N-Bromosuccinimide[0178][0179] To a 0.4 M solution of a methyl-substituted aromatic compound, such as ethyl 4-bromo-3-methylbenzoate, incarbon tetrachloride was added N-bromosuccinimide (1.05 eq) and benzoyl peroxide (0.03 eq), and the mixture washeated at reflux for 8-16 h. The mixture was cooled and filtered and the filtrate concentrated. The residue was purifiedby trituration with 3:1 hexanes/ethyl acetate, or by silica gel chromatography using hexanes/ethyl acetate as eluant toprovide the mono-brominated product, such as ethyl 4-bromo-3-(bromomethyl)benzoate.
57% With N-Bromosuccinimide; dibenzoyl peroxide In acetonitrile at 82℃; for 10h;
45% With N-Bromosuccinimide; dibenzoyl peroxide In Carbon tetrachloride at 80℃; 1.1 Step 1: Synthesis of ethyl 4-bromo-3-(bromomethyl)benzoate (compound 1b) To a solution of compound 1a (5.00 g, 20.57 mmol) in carbon tetrachloride (50 mL) was added NBS (3.84 g, 21.60 mmol) and dibenzoyl peroxide (BPO) (0.4 mL, 2.06 mmol).The reaction was stirred at 80°C until the reaction was complete.After cooling, the mixture was filtered, and the filtrate was concentrated in vacuo.Purified by silica gel column chromatography (eluent: 0-2% ethyl acetate in petroleum ether) to obtain compound 1b (3.00 g, yield 45%)
With N-Bromosuccinimide 275.A A. A. Ethyl 4-bromo-3-(bromomethyl)benzoate Ethyl 4-bromo-3-methylbenzoate (110 g, 450 mmol) was treated with NBS according to the procedure of P2A. Silica gel chromatography with hexanes/ethyl acetate as eluant provided 275A (91 g, 62%) as a white solid.
With N-Bromosuccinimide 275.227.A A. A. Ethyl 4-bromo-3-(bromomethyl)benzoate Ethyl 4-bromo-3-methylbenzoate (110 g, 450 mmol) was treated with NBS according to the procedure of P2A. Silica gel chromatography with hexanes/ethyl acetate as eluant provided 275A (91 g, 62%) as a white solid.
With N-Bromosuccinimide; dibenzoyl peroxide In Carbon tetrachloride at 80℃; for 6h; Halogen lamp; 29.2 Step 2: 4-Bromo-3-bromomethyl-benzoic acid ethyl ester 4-Bromo-3-methyl-benzoic acid ethyl ester (18.24 g, 75.4 mmol), N-bromosuccinimide (14.1 g, 79.2 mmol), and benzoyl peroxide (0.9 g, 3.77 mmol) were combined in CC14, and the reaction was heated to 80° C. and stirred with a halogen desk lamp shining on it for 6 hours. The mixture was concentrated and partitioned between CH2Cl2 and H2O. The organic layer was separated and washed with H2O and brine, and then dried and concentrated. The residue was triturated with hexane (3*50 mL) and dried to give the title compound.
With N-Bromosuccinimide; dibenzoyl peroxide In Carbon tetrachloride at 80℃; for 6h; halogen desk lamp irradition; 1.3 Step 3: 4-Bromo-3-methyl-benzoic acid ethyl ester (18.24 g, 75.4 mmol), N-bromosuccinimide (14.1 g, 79.2 mmol), and benzoyl peroxide (0.9 g, 3.77 mmol) were combined in CCl4, and the reaction was heated to 80° C. and stirred with a halogen desk lamp shining on it for 6 hours. The mixture was concentrated and partitioned between CH2Cl2 and H2O. The organic layer was separated and washed with H2O and brine, and then dried and concentrated. The residue was triturated with hexane (3*50 mL) and dried to give 4-bromo-3-bromomethyl-benzoic acid ethyl ester.
With N-Bromosuccinimide; dibenzoyl peroxide In Carbon tetrachloride at 20℃; for 10h; Heating / reflux; 1.02; 13.03; 14.03; 15.03; 16.04; 20.03; 21.06; 22.03; 23.03; 38.05 STEP02: Synthesis of ethyl 4- bromo-3-(bromo methyl) benzoate.; To the solution of 4-bromo-3 methyl benzoic acid ethyl ester (25 gm, 0.102 mol) in (100 ml) carbon tetrachloride at room temperature was added N-bromosuccinimide (20.13 gm, 0.113 mol) and (1.24 gm, 0.005 mol)benzoyl peroxide. Then the reaction mixture was refluxed for 10 hrs. The reaction mixture was cooled and filtered. The filtrate was concentrated under vacuum. The residue thus obtained was purified by triturating it with (100 ml) hexane. Solid thus obtained was filtered and suction dried to give 12 gm of ethyl 4-bromo-3-(bromo methyl) benzoate.; STEP03: Synthesis of ethyl 4-bromo-3-(bromo methyl) benzoate.; To a solution of 4-bromo-3 -methyl benzoic acid ethyl ester (28 gm,0.11mol) in 100 ml of carbon tetrachloride was added 22.65 gm (0.12 mol) of N-bromosuccinimide and benzoyl peroxide (1.4gm, 0.005mol, 75% in water) and the mixture was refluxed for 10 hrs. The reaction mixture was cooled to room temperature and filtered. The filtrate was then concentrated and the residue thus obtained was purified by triturating with hexane (100 ml) to give the solid product, which was filtered and suction dried to give 17.5 gm of ethyl 4-bromo-3-(bromo methyl)benzoate; STEP03: Synthesis of ethyl 4-bromo-3-(bromo methvDbenzoate.; To a solution of 4-bromo-3 -methyl benzoic acid ethyl ester (28 gm,0.11mol) in 100 ml of carbon tetrachloride was added 22.65 gm (0.12 mol) of N-bromosuccinimide and benzoyl peroxide (1.4gm, 0.005mol, 75% in water) and the mixture was refluxed for 10 hrs. The reaction mixture was cooled to room temperature and filtered and the filtrate was concentrated. The residue thus obtained was purified by triturating with hexane (100 ml) which gave the solid product, which was filtered and suction dried to give 17.5 gm of ethyl 4-bromo-3-(bromo methyl)benzoate; STEP03: Synthesis of ethyl 4-bromo-3-(bromo methyPbenzoate.; To a solution of 4-bromo-3 methyl benzoic acid ethyl ester (28 gm, 0.1 lmol) in 100 ml of carbon tetrachloride was added 22.65 gm (0.12 mol) of N-bromosuccinimide and benzoyl peroxide (1.4gm, 0.005mol, 75% in water) and the mixture was refluxed for 10 hrs. The mixture was then cooled to room temperature and filtered and the filtrate was concentrated. The residue thus obtained was purified by triturating with hexane (100 ml) which gave the solid product, which was filtered and suction dried to give 17.5 gm of ethyl 4-bromo-3- (bromo methyl)benzoate; STEP04: Synthesis of ethyl 4-bromo-3-(bromo methvDbenzoate.; To the solution of 4-bromo-3 methyl benzoic acid ethyl ester (28 gm,0.11mol) in 100 ml of carbon tetrachloride was added (22.65 gm, 0.12 mol) of N-bromosuccinimide and benzoyl peroxide (1.4gm,0.005mol, 75% in water) and the mixture was refluxed for 10 hrs. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and the residue thus obtained was purified by triturating with hexane(100 ml) which gave the solid product, which was filtered and suction dried to give 17.5 gm of ethyl 4-bromo-3-(bromo methyl)benzoate

Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - EP2732818, 2017, B1 Location in patent: Paragraph 0169; 0178; 0179
[2]Han, Jia-Qi; Li, Lin-Ping; Liu, Yun-Ting; Wu, Xiong; Xie, Jian-Hua; Yang, Fan; Zhou, Qi-Lin [Organic Letters, 2022, vol. 24, # 14, p. 2590 - 2595]
[3]Current Patent Assignee: SHANGHAI TUO JIE BIOMEDICAL TECH - CN112876424, 2021, A Location in patent: Paragraph 0138-0143
[4]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US2002/143024, 2002, A1
[5]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - US6638937, 2003, B2
[6]Current Patent Assignee: BRICKELL BIOTECH INC - US2009/197959, 2009, A1 Location in patent: Page/Page column 20; 21
[7]Current Patent Assignee: PAMELA PHARMACEUTICAL - US2010/81673, 2010, A1 Location in patent: Page/Page column 10
[8]Current Patent Assignee: TORRENT INVESTMENTS PRIVATE LIMITED - WO2007/100295, 2007, A1 Location in patent: Page/Page column 33-34; 148; 160; 172; 185; 223; 229; 233; 311
  • 2
  • [ 347852-72-6 ]
  • [ 254740-64-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1.1: ethanol; N,N-dimethyl-formamide / 16 h / 0 - 20 °C 2.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / toluene; ethanol; water / 3 h / 85 °C / Inert atmosphere 3.1: diisobutylaluminium hydride / toluene; tetrahydrofuran / 2 h / -78 - -25 °C 4.1: carbon tetrabromide; triphenylphosphine / N,N-dimethyl-formamide / 4 h / 0 °C 5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / 0 - 20 °C 5.2: 0 - 20 °C 6.1: hydrogenchloride / ethanol; water / 1 h / Reflux
Reference： [1]Current Patent Assignee: LIGAND PHARMACEUTICALS INC - EP2732818, 2017, B1

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