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Chemistry
Organic Building Blocks
Aryls
2-Bromo-5-fluorobenzamide
Chemistry
Organic Building Blocks
Aryls
Amines Bromides Fluorinated Building Blocks Amides

[ CAS No. 1006-34-4 ]

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1006-34-4
Chemical Structure| 1006-34-4
Structure of 1006-34-4 * Storage: {[proInfo.prStorage]}

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Product Details of [ 1006-34-4 ]

CAS No. :1006-34-4 MDL No. :MFCD03094322
Formula : C7H5BrFNO Boiling Point : 249.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :218.02 g/mol Pubchem ID :-
Synonyms :

Safety of [ 1006-34-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P302+P352-P305+P351+P338-P362-P403+P233-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1006-34-4 ]

  • Downstream synthetic route of [ 1006-34-4 ]

[ 1006-34-4 ] Synthesis Path-Downstream   1~14

YieldReaction ConditionsOperation in experiment
/BRN= 575969/, NH3-Lsg.;
  • 2
  • [ 1006-34-4 ]
  • [ 4637-24-5 ]
  • [ 67-56-1 ]
  • 2-bromo-N-((dimethylamino)methylene)-5-fluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% at 120℃; for 1.5h; A mixture of 2-bromo-5-fluorobenzamide (9.50 g, 43.57 mmol) and N,N-dimethylformamide dimethyl acetal (20 ml) was heated under argon at 120° C. for 1.5 h. The methanol formed during the reaction was collected through a reflux condenser. The reaction mixture was allowed to cool and the excess N,N-dimethylformamide dimethyl acetal was removed under reduced pressure. The residual oil was crystallized from a mixture of ether (75 ml) and hexane (50 ml) to give 8.55 g (72% yield) of the title material as white crystals. 1HNMR 400 MHz (CDCl3) δ (ppm): 3.21 (3H, s, CH3), 3.24 (3H, s, CH3), 7.0 (1H, m, aromatic), 7.58 (1H, dd, J=5.0 Hz and J=8.5 Hz, aromatic), 7.64 (1H, dd, J=3.0 Hz and J=9.1 Hz, aromatic), 8.64 (1H, s, CH).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/111984, 2007, A1 Location in patent: Page/Page column 42
  • 3
  • [ 18871-66-4 ]
  • [ 1006-34-4 ]
  • [ 67-56-1 ]
  • 2-bromo-N-(1-(dimethylamino)ethylidene)-5-fluorobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% at 120℃; for 1.5h; A mixture of 2-bromo-5-fluorobenzamide (9.57 g, 43.89 mmol) and N,N-dimethylacetamide dimethyl acetal (20 ml) was heated under argon at 120° C. for 1.5 h. The methanol formed was collected through a reflux condenser. The reaction mixture was allowed to cool and the excess N,N-dimethylacetamide dimethyl acetal was removed under reduced pressure. The residual oil was crystallized from a mixture of ether (30 ml) and hexane (50 ml) to give 9.51 g (75% yield) of the title material as white crystals. 1HNMR 400 MHz (CDCl3) δ (ppm): 2.43 (3H, s, CH3), 3.16 (3H, s, NCH3), 3.19 (3H, s, NCH3), 6.90-6.97 (1H, m, aromatic), 7.46 (1H, dd, J=3.1 Hz and J=9.1 Hz, aromatic), 7.53 (1H, dd, J=5.1 Hz and J=9.1 Hz, aromatic). MS (ESI+) m/e 287 [M+H+].
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/111984, 2007, A1 Location in patent: Page/Page column 43
  • 4
  • [ 111771-13-2 ]
  • [ 1006-34-4 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide In tetrahydrofuran; lithium hydroxide monohydrate at 25℃; for 20h; A solution of 2-bromo-5-fluorobenzoic acid (10.0 g, 45.66 mmol) in dichloromethane (100 ml) was treated at 25° C. with oxalyl chloride (8.0 ml, 91.3 mmol) followed by a drop of N,N-dimethylformamide. The resulting mixture was then stirred for 4 h. The solvent and excess reagent were evaporated in vacuo and the residual oil was dissolved in tetrahydrofuran (100 ml) and added to a mixture of tetrahydrofuran (200 ml ), water (100 ml ) and concentrated ammonium hydroxide (10 ml ). The resulting mixture was then stirred at 25° C. for 20 h. The reaction mixture was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and concentrated to give 9.51 g (96% yield) of the title amide as a white solid. 1HNMR 400 MHz (CDCl3) δ (ppm): 5.9-6.3 (2H, broad, NH2), 7.05 (1H, m, aromatic), 7.42 (1H, dd, J=3.2 Hz and J=8.3 Hz, aromatic), 7.61 (1H, dd, J=5.1 Hz and J=9.1 Hz, aromatic).
With ammonium hydroxide In dichloromethane at 0 - 20℃; for 1h;
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US2007/111984, 2007, A1 Location in patent: Page/Page column 41-42
[2]Hoque, Md Emdadul; Bisht, Ranjana; Unnikrishnan, Anju; Dey, Sayan; Mahamudul Hassan, Mirja Md; Guria, Saikat; Rai, Rama Nand; Sunoj, Raghavan B.; Chattopadhyay, Buddhadeb [Angewandte Chemie - International Edition, 2022, vol. 61, # 27][Angew. Chem., 2022, vol. 134, # 27]
  • 5
  • [ 394-28-5 ]
  • [ 1006-34-4 ]
YieldReaction ConditionsOperation in experiment
94.7% To a RB flask equipped with an addition funnel is charged acid 7, 2-Me-THF and DMF. The solution is then cooled to 70C and oxalyl chloride is added dropwise over 30 min at < 15 0C.After the addition is complete, the reaction mixture is warmed to it and aged for 45 min. Upon complete consumption of the acid, the reaction mixture is then charged dropwise into another flask containing cold (9 0C) mixture of concentrated NH4OH and 2-Me-THF over 1.5 h, while maintaining the temperature around 20-250C. To the reaction mixture is added water (100 mL)15 to dissolve some solids and the resulting biphasic layer is transferred to a separatory funnel. The aqueous layer is separated and the organic layer is washed with 1 N HCl (50 mL) and with brine (100 mL). The final organic layer is then solvent switched to toluene to give a final slurry concentration of 15 vol. The slurry is then hheated to 110 0C to get a clear solution, which is then cooled slowly to RT. Crystallization is typically observed to occur at 1000C and after aging at rt overnight, heptane (10 vol) is then added, followed by a Ih of age. The suspension is then filtered and the wet cake is washed with cold 1 :1 heptane :toluene and dried under a stream of N2 to give the product in 46.9 g (94.7%).
94.7% To a RB flask equipped with an addition funnel is charged acid 7a, 2-Me-THF and DMF. The solution is then cooled to 70C and oxalyl chloride is added dropwise over 30 min at < 15 0C. After the addition is complete, the reaction mixture is warmed to rt and aged for 45 min. Upon complete consumption of the acid, the reaction mixture is then charged dropwise into another flask containing cold (9 0C) mixture of concentrated NH4OH and 2-Me-THF over 1.5 h, while maintaining the temperature around 20-250C. To the reaction mixture is added water (100 mL) to dissolve some solids and the resulting biphasic layer is transferred to a separatory funnel. The aqueous layer is separated and the organic layer is washed with 1 N HCl (50 mL) and with brine (100 mL). The final organic layer is then solvent switched to toluene to give a final slurry concentration of 15 vol. The slurry is then hheated to 1 10 0C to get a clear solution, which is then <n="17"/>cooled slowly to RT. Crystallization is typically observed to occur at 1000C and after aging at rt overnight, heptane (10 vol) is then added, followed by a Ih of age. The suspension is then filtered and the wet cake is washed with cold 1 :1 heptane:toluene and dried under a stream of N2 to give the product in 46.9 g (94.7%).
Reference： [1]Patent: WO2008/51532,2008,A1 .Location in patent: Page/Page column 59-60
[2]Patent: WO2009/54925,2009,A1 .Location in patent: Page/Page column 15-16
  • 6
  • [ 754235-83-1 ]
  • [ 1006-34-4 ]
  • [ 1021539-61-6 ]
YieldReaction ConditionsOperation in experiment
95% With piperidine; tri tert-butylphosphoniumtetrafluoroborate In acetonitrile at 80℃; for 3 - 4h; 1.3 Alkyne 4a, bromide 5a, acetonitrile (PvM Table, line 6), and piperidine are charged successively to a round bottom flask equipped with a thermocouple, stir bar, and reflux condenser. The reagents are stirred until a reddish-brown solution is formed and the solution is degassed by 5 vacuum and nitrogen refill cycles. The phosphine ligand and palladium catalyst are then added successively and the resulting solution is degassed again. The solution is then heated to 80 °C and aged until a 99% conversion by HPLC analysis is achieved (typically 1 h). The solution is diluted with 100 mL of toluene and is then washed successively with HOAc (1.5 equiv) in 15 wt% aqueous NaCl (48 mL), saturated KHCO3 solution (40 mL), and saturated NaCl solution (40 mL). Ecosorb 941 (2.53 g) and trithiocyanuric acid (127 mg) are added to the solution and the solution was stirred between 23-25 °C for 1 hour. The black slurry is then filtered over Solka flock (10 g) through a 15-20 micron fritted funnel. The wet cake is washed with 130 mL of 2:1 toluene: CH3 CN. The solution is transferred to a separatory funnel and washed with 15 wt%K2CO3 aqueous solution (38 mL) and then diluted with toluene (26.7 mL) and CH3CN (53 mL). The organic layer is washed with saturated aqueous NaCl (38 mL) and transferred to a round bottom flask. The organic layer is assayed to contain 12.76 gA of product 6a by HPLC analysis.
92% With piperidine In acetonitrile at 80℃; for 3 - 4h; 159.3; 159.4 Alkyne 4, bromide 5, acetonitrile (RM Table, line 6), and piperidine are charged successively to a round bottom flask equipped with a thermocouple, stir bar, and reflux condenser. The reagents are stirred until a reddish-brown solution is formed and the solution is degassed by 5 vacuum and nitrogen refill cycles. The phosphine ligand and palladium catalyst are then added successively and the resulting solution is degassed again. The solution is then heated to 80 0C and aged until a 99% conversion by HPLC analysis is achieved (typically 1 h). The solution is diluted with 100 mL of toluene and is then washed successively with HOAc (1.5 equiv) in 15 wt% aqueous NaCl (48 mL), saturated KHCO3 solution (40 mL), and saturated NaCl solution (40 mL). Ecosorb 941 (2.53 g) and trithiocyanuric acid (127 mg) are added to the solution and the solution was stirred between 23-25 °C for 1 hour. The black slurry is then filtered over Solka flock (10 g) through a 15-20 micron fritted funnel. The wet cake is washed with 130 mL of 2:1 toluene:CH3CN. The solution is transferred to a separatory funnel and washed with 15 wt% K2CO3 aqueous solution (38 mL) and then diluted with toluene (26.7 mL) and CH3CN (53 mL). The organic layer is washed with saturated aqueous NaCl (38 mL) and transferred to a round bottom flask. The organic layer is assayed to contain 12.76 gA of product 6 by HPLC analysis. The crude solution of 6 (12.6 g) in PhMe/MeCN is concentrated under reduced pressure to remove MeCN, while maintaining the total volume of lOvol and the batch temperature at 20-25 0C. Total of 6-vol of PhMe is used during this process. At the end of the solvent switch, the resulting slurry is heated up to 90 0C and cooled slowly to 720C. After appropriate seeding, the product started to crystallize to give a slurry which is then aged overnight. Heptane (3.3 vol) is then added and the resulting mixture is aged until 6-8% of product remained in the mother liquor. At this point, the slurry is then filtered and the wetcake is washed with cold PhMe/Heptane (3/1, 6 vol) followed by heptane (3 vol) and dried under stream of N2 overnight. The product is isolated as pale yellow solid in 13.67 g (84.4 wt%) in 92% recovery or 81% overall yield.
Reference： [1]Current Patent Assignee: MERCK & CO INC - WO2009/54925, 2009, A1 Location in patent: Page/Page column 13-14
[2]Current Patent Assignee: MERCK & CO INC - WO2008/51532, 2008, A1 Location in patent: Page/Page column 57-58
  • 7
  • [ 5390-04-5 ]
  • [ 1006-34-4 ]
  • [ 1255775-75-7 ]
YieldReaction ConditionsOperation in experiment
13% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
Reference： [1]Okamoto, Noriko; Takeda, Kei; Yanada, Reiko [Journal of Organic Chemistry, 2010, vol. 75, # 22, p. 7615 - 7625]
  • 8
  • [ 1006-34-4 ]
  • [ 693-02-7 ]
  • [ 1207252-51-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 19.5 h / 50 °C / Inert atmosphere 2: [bis(acetoxy)iodo]benzene; platinum(II) chloride / 1,2-dichloro-benzene / 2 h / 100 °C
Reference： [1]Okamoto, Noriko; Miwa, Yoshihisa; Minami, Hideki; Takeda, Kei; Yanada, Reiko [Angewandte Chemie - International Edition, 2009, vol. 48, # 51, p. 9693 - 9696]
  • 9
  • [ 1006-34-4 ]
  • [ 693-02-7 ]
  • [ 1207252-46-7 ]
YieldReaction ConditionsOperation in experiment
54% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 50℃; for 19.5h; Inert atmosphere;
Reference： [1]Okamoto, Noriko; Miwa, Yoshihisa; Minami, Hideki; Takeda, Kei; Yanada, Reiko [Angewandte Chemie - International Edition, 2009, vol. 48, # 51, p. 9693 - 9696]
  • 10
  • [ 1006-34-4 ]
  • [ 536-74-3 ]
  • [ 1338797-90-2 ]
YieldReaction ConditionsOperation in experiment
50% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; Microwave irradiation; Inert atmosphere;
Reference： [1]Long, Yuhua; She, Zhigang; Liu, Xiaochen; Chen, Yu [Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2579 - 2588]
  • 11
  • [ 1006-34-4 ]
  • [ 768-60-5 ]
  • [ 1425605-66-8 ]
YieldReaction ConditionsOperation in experiment
45% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In N,N-dimethyl-formamide at 120℃; for 3h; Microwave irradiation; Inert atmosphere;
Reference： [1]Long, Yuhua; She, Zhigang; Liu, Xiaochen; Chen, Yu [Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2579 - 2588]
  • 12
  • [ 33184-16-6 ]
  • [ 1006-34-4 ]
Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 2579 - 2588
  • 13
  • [ 1006-34-4 ]
  • [ 1425605-95-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 3 h / 120 °C / Microwave irradiation; Inert atmosphere 2: ammonium acetate; sodium tetrachloroaurate(III) dihydrate; silver hexafluoroantimonate / acetonitrile / 20 h / 85 °C
Reference： [1]Long, Yuhua; She, Zhigang; Liu, Xiaochen; Chen, Yu [Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2579 - 2588]
  • 14
  • [ 1006-34-4 ]
  • [ 1425606-02-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 3 h / 120 °C / Microwave irradiation; Inert atmosphere 2: ammonium acetate; sodium tetrachloroaurate(III) dihydrate; silver hexafluoroantimonate / acetonitrile / 20 h / 85 °C
Reference： [1]Long, Yuhua; She, Zhigang; Liu, Xiaochen; Chen, Yu [Journal of Organic Chemistry, 2013, vol. 78, # 6, p. 2579 - 2588]

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