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Chemical Structure| 881676-32-0 Chemical Structure| 881676-32-0

Structure of 881676-32-0

Chemical Structure| 881676-32-0

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Product Details of [ 881676-32-0 ]

CAS No. :881676-32-0
Formula : C5H4BrNO
M.W : 174.00
SMILES Code : O=CC1=CNC(Br)=C1
MDL No. :MFCD11875943
InChI Key :XTLHTMDWLYWDEO-UHFFFAOYSA-N
Pubchem ID :57831983

Safety of [ 881676-32-0 ]

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

Application In Synthesis of [ 881676-32-0 ]

* 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 [ 881676-32-0 ]

[ 881676-32-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 881676-32-0 ]
  • [ 445-29-4 ]
  • [ 881674-56-2 ]
YieldReaction ConditionsOperation in experiment
96.5% With bis-triphenylphosphine-palladium(II) chloride; 1,10-Phenanthroline; copper (I) acetate; sodium hydroxide; In dimethyl sulfoxide; at 140℃; for 5h;Inert atmosphere; Dimethyl sulfoxide (200 mL) was added to a 500 mL three-neck flask, and 2-fluorobenzoic acid (II) (14.2 g, 0.1 mol) was added under nitrogen.5-bromopyrrole-3-carbaldehyde (III) (35.5 g, 0.2 mol), sodium hydroxide (40.1 g, 1 mol), Pd(PPh3)2Cl2 (14.1 g, 0.02 mol), CuOAc (4.9 g, 0.04 mol) ,1,10-Phenanthroline (7.3g, 0.04mol), stirring, heating to 140C, reaction for 5h,The reaction was completed by HPLC (2-fluorobenzoic acid (II) content is less than 1%), the temperature was lowered to 20C, the pH was adjusted to 6 with 5% aqueous hydrochloric acid solution, and the solid was slowly precipitated by adding water.The solid was extracted with ethyl acetate (50 mL X 3).The resulting organic phase was washed with saturated sodium bicarbonate solution (100 mL) and saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to 80 g and re-crystallized by the dropwise addition of petroleum ether (150 mL).Filtration drying gave a reddish solid product (18.5 g, yield: 96.5% based on 2-fluorobenzoic acid (II)).
  • 2
  • [ 881676-32-0 ]
  • [ 1993-03-9 ]
  • [ 881674-56-2 ]
YieldReaction ConditionsOperation in experiment
82.8% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere; Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, 19.0 g (0.136 mol) of 2-fluorophenylboronic acid, 15.0 g of potassium carbonate in a four-necked flask, and add 100 g of DMF and 40 g of water in a nitrogen atmosphere. A catalytic amount of tetrakis(triphenylphosphine)palladium was added thereto, and the temperature was raised to 105 C, and the reaction was carried out for 20 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with water, and extracted with ethyl acetate. The extract was dried, suction filtered, concentrated and weighed. Crystallization gave 13.5 g of gray solid 1, yield 82.8%, purity 99.94%
82.8% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; N,N-dimethyl-formamide; at 105℃; for 20h;Inert atmosphere; Weigh 15.0 g (0.086 mol) of 5-bromopyrrole-3-carbaldehyde, respectively.19.0 g (0.136 mol) of 2-fluorophenylboronic acid,15.0g of potassium carbonate in a four-necked bottle,Add 100g DMF and 40g water,A catalytic amount of tetrakis(triphenylphosphine)palladium is added under a nitrogen atmosphere.Warming up to 105 C,Reaction for 20h,After the reaction is over,Down to room temperature,Dilute with water,Extracted with ethyl acetate,The extract is dried,Filtering,concentrate,Recrystallization gave 13.5 g of a gray solid 1,The yield is 82.8%.Purity 99.94%,
 

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