Home Cart 0 Sign in  

[ CAS No. 106614-28-2 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 106614-28-2
Chemical Structure| 106614-28-2
Structure of 106614-28-2 * Storage: {[proInfo.prStorage]}

Quality Control of [ 106614-28-2 ]

Related Doc. of [ 106614-28-2 ]

SDS
Alternatived Products of [ 106614-28-2 ]
Alternatived Products of [ 106614-28-2 ]

Product Details of [ 106614-28-2 ]

CAS No. :106614-28-2 MDL No. :MFCD03093799
Formula : C8H6F2O2 Boiling Point : 198.8°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :172.13 g/mol Pubchem ID :2782897
Synonyms :

Safety of [ 106614-28-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 106614-28-2 ]

  • Upstream synthesis route of [ 106614-28-2 ]
  • Downstream synthetic route of [ 106614-28-2 ]

[ 106614-28-2 ] Synthesis Path-Upstream   1~24

  • 1
  • [ 106614-28-2 ]
  • [ 56456-47-4 ]
Reference: [1] Tetrahedron Letters, 2004, vol. 45, # 31, p. 6021 - 6022
  • 2
  • [ 106614-28-2 ]
  • [ 125568-71-0 ]
YieldReaction ConditionsOperation in experiment
1.8 g at 20℃; for 0.5 h; 0.80mL fuming nitric acid was added dropwise 5mL concentrated sulfuric acid, stirred for 5min,Methyl 2,4-difluorobenzoate was added dropwise(1.50g, 8.71mmol, 1.0eq), and then reacted at room temperature for 30min, poured into ice water to precipitate a white solid, which was suction filtered to give a white solidProducts, dry, white solid product 1.8g.
Reference: [1] Patent: US2004/220235, 2004, A1,
[2] Patent: CN106749233, 2017, A, . Location in patent: Paragraph 0203; 0204
  • 3
  • [ 865-33-8 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 4
  • [ 124-41-4 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 5
  • [ 865-33-8 ]
  • [ 106614-28-2 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 6
  • [ 865-34-9 ]
  • [ 106614-28-2 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 7
  • [ 124-41-4 ]
  • [ 106614-28-2 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 8
  • [ 865-34-9 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 9
  • [ 865-33-8 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 2150-41-6 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 10
  • [ 124-41-4 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 2150-41-6 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 11
  • [ 1583-58-0 ]
  • [ 106614-28-2 ]
YieldReaction ConditionsOperation in experiment
97% With thionyl chloride In methanol 1
methyl 2,4-difluorobenzoate
A solution of 2,4-difluorobenzoic acid (1.5808 g, 10.00 mmol) in methanol (15 ml) was cooled to 0° C. in ice-water bath.
To the mixture was added dropwise a solution of thionyl chloride (1.46 ml, 20.02 mmol) in methanol (10 ml).
The mixture was gradually warmed to room temperature and stirred for 24 hours.
The mixture was added to sat.
NaHCO3 aqueous solution, extracted three times with ether and dried over MgSO4.
The mixture was concentrated and purified by silica gel chromatography (hexane/ether=5/1) to give the title compound (1.6743 g; 97percent).
1H-NMR(CDCl3) 7.99 (td, 1H, J=8.2, 6.6 Hz), 6.98-6.84 (m, 2H), 3.93 (s, 3H)
Reference: [1] Patent: US6194461, 2001, B1,
  • 12
  • [ 67-56-1 ]
  • [ 72482-64-5 ]
  • [ 106614-28-2 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 2 h; To 100 mL of MeOH, 2,4-difluorobenzoyl chloride (10 mL, 79.3 mmol) was added and the mixture stirred at room temperature for 2 hours. The solvent was then evaporated affording the tilte compound as pale yellow oil (quantitative).IH-NMR (400 MHz), δ (ppm, DMSOtZ6): 8.0 (m, IH), 7.44 (m, IH), 7.25 (m, IH),3.87 (s, 3H).
100% at 20℃; for 2 h; Stcp i; Preparation of 2,4-difluoro-benzoic acid methyl ester; To 100 mL of methanol, 2,4-difluoro-benzoyl chloride (10 mL, 79.3 mrno.) was added and the mixture stirred at room temperature for 2 hours. The solvent was then evaporated affording the title compound as pale yellow oii (quantitative).1 H-NMR {400 MHz), USD (ppm, DMSO-cfe): 8,0 (m, 1H), 7-44 (m, 1H), 725 (m, 1H), 3.87 (S, 3H).
Reference: [1] Patent: WO2007/68619, 2007, A1, . Location in patent: Page/Page column 97
[2] Patent: WO2007/99171, 2007, A2, . Location in patent: Page/Page column 53
  • 13
  • [ 67-56-1 ]
  • [ 1583-58-0 ]
  • [ 106614-28-2 ]
YieldReaction ConditionsOperation in experiment
88 g at 60℃; for 8 h; Sulphuric acid (97.4g) was added to a mixture of 2,4-diflourobenzoic acid (100 g) and methanol (1 L) at ambient temperature. The reaction mixture was heated to 60°C and maintained at that temperature for 8 hours. After cooling to room temperature, water (500 mL) was added. The reaction mixture was slowly added to chilled water (500 mL). The organic layer was separated and the aqueous layer was thrice extracted with dichloromethane (500 mL x 3). The combined dichloromethane layers were washed with 10percent sodium bicarbonate solution (200 mL) then concentrated under vacuum at temperature of not more than (NMT) 50-55°C to give methyl 2,4-difluorobenzo ate (88 g, Yield: 0.8w/w).
Reference: [1] Journal of Agricultural and Food Chemistry, 2012, vol. 60, # 4, p. 1036 - 1041
[2] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 29
  • 14
  • [ 67-56-1 ]
  • [ 15226-74-1 ]
  • [ 106614-28-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425
  • 15
  • [ 124-38-9 ]
  • [ 2265-93-2 ]
  • [ 74-88-4 ]
  • [ 106614-28-2 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4314 - 4317
  • 16
  • [ 67-56-1 ]
  • [ 15226-74-1 ]
  • [ 106614-28-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425
  • 17
  • [ 367-27-1 ]
  • [ 106614-28-2 ]
Reference: [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 3, p. 419 - 425
  • 18
  • [ 865-33-8 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3776 - 3779
  • 19
  • [ 124-41-4 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 20
  • [ 865-34-9 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 21
  • [ 865-33-8 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 2150-41-6 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 22
  • [ 124-41-4 ]
  • [ 106614-28-2 ]
  • [ 128272-26-4 ]
  • [ 2150-41-6 ]
  • [ 204707-42-6 ]
Reference: [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044
  • 23
  • [ 98549-88-3 ]
  • [ 106614-28-2 ]
  • [ 1235865-75-4 ]
YieldReaction ConditionsOperation in experiment
76.5% With potassium phosphate In diethylene glycol dimethyl ether at 110℃; for 24 h; To a three-necked flask was added 100 g of 5-hydroxy-7-azaindole (746 mmol), 141 g of methyl 2,4-difluorobenzoate(821 mmol), 237 g of potassium phosphate (1.12 mol) and 500 mL of diethylene glycol dimethyl Ether, 110 ° C for 24 h (HPLC to monitor 5-hydroxy-7-azaindole).The reaction solution was concentrated to dryness, and 2L of ethyl acetate and 2 L of water were added. The organic phase was separated,dried over anhydrous sodium sulfate, and concentrated to dry crude.The crude product was heated to reflux with 1260 mL of ethyl acetate. The mixture was slowly added dropwise to a solution of 1260 mL ofpetroleum ether. After 1 h of dropping, the mixture was stirred for 1 h, slowly cooled to 25 ° C, filtered and dried to give163g of pale white solidRate of 76.5percent.HPLC purity 98percent.
62% With potassium phosphate In diethylene glycol dimethyl ether at 115℃; for 10 h; Inert atmosphere Under a nitrogen atmosphere,1H-pyrrolo[2,3-b]pyridin-5-ol (1.0 g, 7.45 mmol), Methyl 2,4-difluorobenzoate (1.6 g, 9.31 mmol), Potassium phosphate (2.05g, 9.69mmol)Add to 20mL diglyme solution,The reaction solution was stirred at 115 ° C for about 10 h.Plate analysis until the starting material is completely reacted.The reaction solution was cooled to room temperature, then quenched with water and ethyl acetate.Collect organic phase,Purification by column chromatography gave a white solid product (1.3 g).The yield was 62percent.
22.2% With potassium phosphate heptahydrate In diethylene glycol dimethyl ether at 115℃; Inert atmosphere 1H-pyrrolo [2,3-b] pyridin-5-ol(1.20 g, 8.95 mmol, 1.03 eq) and methyl 2,4-difluorobenzoate (1.5 g, 8.71 mmol, 1.0 eq) were added to 20 mL of diethylene glycol dimethyl ether, followed by addition of potassium phosphate heptahydrate (3.5 G,14.0 mmol, 1.6 eq) under nitrogen atmosphere at 115 ° C overnight. TLC point plate analysis, as well as raw materials, most of which produce ortho products. TLC point plate analysis, as well as raw materials, add 0.3g 2,4-difluorobenzoic acid methyl ester and 0.5g potassium phosphate heptahydrate, continue to react overnight. And then TLC point board analysis, the effect is not very good, as well as raw materials. (30 mL × 3), the organic phase was dried with anhydrous sodium sulfate, spin-dried column, PE / EA (v / v) = 3/1 column, white Solid 525mg. Yield 22.2percent.
588 mg With potassium phosphate In 1,4-dioxane at 34 - 90℃; for 47 h; To a mixture of methyl 2,4-difluoro benzoate (1.0 g) in 1,4-dioxane (20 mL), 5-hydroxypyrrolo[2,3-b]pyridine (779 mg) and K3P04 (1.47 g) were added at 34°C and heated to90°C. The reaction mixture is stirred at the same temperature for 23 hours. K3P04 (396mg) was added at 90°C to the reaction mixture and stirred for another 24 hours at thesame temperature. Cooled the reaction mixture to 32°C and filtered on a celite bed.Washed the celite bed with ethyl acetate (20 mL) and evaporated the solvent in the filtrateto obtain crude product. The crude product was purified by column chromatography using60-120 silica gel mesh and 10-50percent ethyl acetate- hexane as eluent to obtain the titlecompound as white solid. Yield: 588 mg; Purity by HPLC: 98.73percent
80 g With potassium phosphate In diethylene glycol dimethyl ether at 110℃; A mixture of formula 8 (R=methyl and X=F, 100 g), formula 7 (152 g), potassium phosphate (190 g),and diglyme were stirred at 1 1 Ο°C for 20-22 hours. Afte r cooling, the reaction mixture was filtered through a Celite bed and the filtrate was washed with diglyme (150 mL). Activated carbon (10 g) was charged and the mixture was stirred for 1 hour. The reaction mass was filtered through a Celite bed and the filtrate was washed with diglyme. Water (3000 mL)was added to the mother liquor and the mixture was stirred at 0- 5°C for 2 hours. The mixture was then filtered and the obtained solid was washed with water (450 mL) then dried at 60°C under vacuum. Toluene was added and the mixture was stirred at 80°C. After cooling to 0-5°C, the reaction mixture stirred for 2 hours, filtered, and the obtained solid was washed with chilled toluene. The solid was suck dried then dried under vacuum (50mm Hg) at 50 (80g, Yield: 0.8 w/w).

Reference: [1] Patent: CN107089981, 2017, A, . Location in patent: Paragraph 0033; 0034; 0035; 0036
[2] Patent: CN108658983, 2018, A, . Location in patent: Paragraph 0110; 0111; 0112
[3] Patent: CN106565706, 2017, A, . Location in patent: Paragraph 0188; 0189; 0190
[4] Patent: WO2017/212431, 2017, A1, . Location in patent: Page/Page column 57; 58
[5] Patent: WO2018/29711, 2018, A2, . Location in patent: Page/Page column 32; 33
  • 24
  • [ 106614-28-2 ]
  • [ 685514-01-6 ]
  • [ 1235865-75-4 ]
Reference: [1] Patent: US2010/184766, 2010, A1, . Location in patent: Page/Page column 56
[2] Patent: US2010/305122, 2010, A1, . Location in patent: Page/Page column 119
[3] Patent: WO2011/150016, 2011, A1, . Location in patent: Page/Page column 80
[4] Patent: WO2012/71336, 2012, A1, . Location in patent: Page/Page column 11
[5] Patent: US2014/275082, 2014, A1, . Location in patent: Paragraph 0228
[6] Patent: WO2016/24230, 2016, A1, . Location in patent: Paragraph 00746
Historical Records

Related Functional Groups of
[ 106614-28-2 ]

Fluorinated Building Blocks

Chemical Structure| 197516-57-7

[ 197516-57-7 ]

Methyl 2-fluoro-6-methylbenzoate

Similarity: 0.98

Chemical Structure| 20372-66-1

[ 20372-66-1 ]

Methyl 2,4,5-trifluorobenzoate

Similarity: 0.96

Chemical Structure| 108928-00-3

[ 108928-00-3 ]

Ethyl 2,4-difluorobenzoate

Similarity: 0.96

Chemical Structure| 586374-04-1

[ 586374-04-1 ]

Methyl 2-fluoro-3-methylbenzoate

Similarity: 0.96

Chemical Structure| 85070-58-2

[ 85070-58-2 ]

Methyl 2-fluoro-4-formylbenzoate

Similarity: 0.96

Aryls

Chemical Structure| 197516-57-7

[ 197516-57-7 ]

Methyl 2-fluoro-6-methylbenzoate

Similarity: 0.98

Chemical Structure| 20372-66-1

[ 20372-66-1 ]

Methyl 2,4,5-trifluorobenzoate

Similarity: 0.96

Chemical Structure| 108928-00-3

[ 108928-00-3 ]

Ethyl 2,4-difluorobenzoate

Similarity: 0.96

Chemical Structure| 586374-04-1

[ 586374-04-1 ]

Methyl 2-fluoro-3-methylbenzoate

Similarity: 0.96

Chemical Structure| 85070-58-2

[ 85070-58-2 ]

Methyl 2-fluoro-4-formylbenzoate

Similarity: 0.96

Esters

Chemical Structure| 197516-57-7

[ 197516-57-7 ]

Methyl 2-fluoro-6-methylbenzoate

Similarity: 0.98

Chemical Structure| 20372-66-1

[ 20372-66-1 ]

Methyl 2,4,5-trifluorobenzoate

Similarity: 0.96

Chemical Structure| 108928-00-3

[ 108928-00-3 ]

Ethyl 2,4-difluorobenzoate

Similarity: 0.96

Chemical Structure| 586374-04-1

[ 586374-04-1 ]

Methyl 2-fluoro-3-methylbenzoate

Similarity: 0.96

Chemical Structure| 85070-58-2

[ 85070-58-2 ]

Methyl 2-fluoro-4-formylbenzoate

Similarity: 0.96