[ CAS No. 6451-86-1 ]

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2D
Chemical Structure| 6451-86-1
Chemical Structure| 6451-86-1
Structure of 6451-86-1

Quality Control of [ 6451-86-1 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 6451-86-1 ]

SDS

Product Details of [ 6451-86-1 ]

CAS No. :6451-86-1MDL No. :MFCD00666893
Formula :C15H13BrO3Boiling Point :427.5°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :321.17Pubchem ID :10903319
Synonyms :

Computed Properties of [ 6451-86-1 ]

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : 3.5 H-Bond Donor Count : 0
SP3 : 0.13 Rotatable Bond Count : 5

Safety of [ 6451-86-1 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6451-86-1 ]

  • Upstream synthesis route of [ 6451-86-1 ]

[ 6451-86-1 ] Synthesis Path-Upstream   1~16

  • 1
  • [ 2973-59-3 ]
  • [ 100-39-0 ]
  • [ 6451-86-1 ]
YieldReaction ConditionsOperation in experiment
98% at 25℃; for 5.00 h; Inert atmosphere 2-bromo-5-hydroxy-4-methoxybenzaldehyde and then a 2 g (8.70 mmol) under a nitrogen condition dissolved in N, N- dimethylformamide, 87 mL (0.1 M), 1.8 g of potassium carbonate at 0oC (13.1 mmol), benzyl bromide 1.77 g (10.4 mmol) were added sequentially. .After the reaction temperature raised to 25 ° C, and reacted for 5 hours. It was added to 100 mL of ammonium chloride aqueous solution to terminate the reaction and extracted with EtOAc (3 × 30 mL). Washing the organic layer with brine (brine, 10 mL × 2), dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by silica gel column chromatography to give the title compound 5- (benzyloxy) -2-bromo-4-methoxybenzaldehyde 2.73 g (8.53 mmol, 98percent).
83% With potassium carbonate In acetonitrile at 50℃; for 20.00 h; 2-Bromo-5-hydroxy-4-methoxybenzaldehyde (25 g, 0.108 mol) and K2CO3 (30 g, 0.216 mol) were added to acetonitrile (250 mL) and flushed with Ar. Benzyl bromide (20 g, 0.12 mol) was added and the mixture was heated under Ar for 20 h at 50° C.
After cooling, the mixture was poured into water (200 ml) and extracted with CH2Cl2 (300 mL).
The CH2Cl2 was washed with water (3*100 mL), dried and concentrated.
Recrystallization with isopropanol: water (3:1) gave 28.8 g (83percent) of 2 as a light brown solid. 1H-NMR (400 MHz, CDCl3) dH 3.96 (3H, s, OCH3), 5.16 (2H, s, CH2Ph), 7.07-7.48 (7H, m, ArH+CH2Ph), 10.16 (1H, s, CHO).
67.9% With potassium carbonate In N,N-dimethyl-formamide at 20℃; To a solution 2-bromo-5-hydroxy-4-methoxybenzaldehyde (1c) (120 g, 520 mmol) in DMF (1000 mL) was added potassium carbonate (79 g, 572 mmol) and benzyl bromide (68 mL, 572 mmol). The reaction mixture was stirred at room temperature overnight and quenched with water (3000 mL). The solid obtained was collected by filtration, washed with ether and dried under vacuum to furnish 5-(benzyloxy)-2-bromo-4-methoxybenzaldehyde (1d) (113.19 g, 67.9percent) as a white solid, MP 144 °C; 1HNMR (300 MHz, DMSO-c/6): δ 10.06 (s, 1H), 7.47- 7.34 (m, 7H), 5.17 (s, 2H), 3.92 (s, 3H); IR (KBr) 2898, 2851 , 1673, 1592, 1502, 1437, 1402, 1264, 1210, 1158, 1017, 754 cm"1; Analysis calculated for C 5H13Br03: C, 56.10; H, 4.08; Found: C, 55.44; H, 4.08.
Reference: [1] Patent: KR101492960, 2015, B1. Location in patent: Paragraph 0092-0094
[2] Tetrahedron, 2006, vol. 62, # 51, p. 12098 - 12107
[3] Journal of Medicinal Chemistry, 2003, vol. 46, # 8, p. 1289 - 1292
[4] Patent: US2006/257337, 2006, A1. Location in patent: Page/Page column 16-17
[5] Patent: WO2016/29214, 2016, A1. Location in patent: Page/Page column 145
[6] Synthesis (Germany), 2018, vol. 50, # 17, p. 3408 - 3419
  • 2
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YieldReaction ConditionsOperation in experiment
87% With potassium phosphate; copper(l) iodide; 1,10-Phenanthroline In 1,4-dioxane at 80℃; Schlenk technique General procedure: In an oven dried Schlenk tube, were added alcohol 1 (69.0–199.5 mg, 0.5 mmol), CuI (10 molpercent)and 1,10-Phenanthroline (20 molpercent) and K3PO4 (2 mmol) followed by the addition of dioxane (2mL) at room temperature under open air atmosphere. The stirred reaction mixture was heated inan oil bath at 80 C for 7–48 h. Progress of the reaction was monitored by TLC till the reaction iscompleted. Then, the reaction mixture was cooled to room temperature, quenched with aqueousNH4Cl solution and then extracted with CH2Cl2 (3 10 mL). The organic layer was washed withsaturated NaCl solution, dried (Na2SO4), and filtered. Evaporation of the solvent under reducedpressure and purification of the crude material by silica gel column chromatography (petroleumether/ethyl acetate) furnished the aldehyde/ketone 2 (61–97percent).
Reference: [1] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
  • 3
  • [ 2973-59-3 ]
  • [ 100-44-7 ]
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YieldReaction ConditionsOperation in experiment
34.2g With potassium carbonate In acetonitrile at 80℃; for 15.00 h; To a solution of 2-bromo-5-hydroxy-4-methoxy-benzaldehyde (25 g, 108 mmol) in MeCN (500 mL) was added (chloromethyl)benzene (13.7 g, 108 mmol) and potassium carbonate (29.9 g, 216 mmol). The mixture was heated at 80 °C with stirring for 15 hours. After being cooledrt, the mixture was filtered. The filtrate was concentrated under reduced pressure. The residuewas partitioned between brine and DCM. The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to give 5 -(benzyloxy)-2-bromo-4-methoxy- benzaldehyde (34.2 g, 96.9 mmol) which was used in the next step without further purification.
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1067 - 1076
[2] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2583 - 2591
[3] Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 2920 - 2928
[4] Patent: WO2017/17043, 2017, A1. Location in patent: Page/Page column 27; 28
  • 4
  • [ 621-59-0 ]
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Reference: [1] Journal of the American Chemical Society, 2006, vol. 128, # 22, p. 7136 - 7137
[2] Journal of Organic Chemistry, 2004, vol. 69, # 9, p. 2920 - 2928
[3] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 10, p. 1512 - 1513
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 931 - 936
[5] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2583 - 2591
[6] Synthesis (Germany), 2018, vol. 50, # 17, p. 3408 - 3419
  • 5
  • [ 6346-05-0 ]
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Reference: [1] Synthetic Communications, 2008, vol. 38, # 13, p. 2138 - 2149
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 931 - 936
[3] Chemical and Pharmaceutical Bulletin, 1999, vol. 47, # 10, p. 1512 - 1513
[4] Organic and Biomolecular Chemistry, 2005, vol. 3, # 5, p. 732 - 734
[5] Organic and biomolecular chemistry, 2003, vol. 1, # 10, p. 1701 - 1706
[6] Journal of the American Chemical Society, 2006, vol. 128, # 22, p. 7136 - 7137
[7] Patent: US2006/9640, 2006, A1. Location in patent: Page/Page column 3; 6
[8] Patent: US5969140, 1999, A
[9] Synlett, 2009, # 7, p. 1041 - 1046
  • 6
  • [ 40705-20-2 ]
  • [ 77-78-1 ]
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Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1067 - 1076
  • 7
  • [ 5392-10-9 ]
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Reference: [1] Tetrahedron, 2006, vol. 62, # 51, p. 12098 - 12107
  • 8
  • [ 120-14-9 ]
  • [ 6451-86-1 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 51, p. 12098 - 12107
  • 9
  • [ 15930-53-7 ]
  • [ 6451-86-1 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1067 - 1076
[2] Patent: WO2016/29214, 2016, A1
  • 10
  • [ 100-44-7 ]
  • [ 6451-86-1 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 931 - 936
  • 11
  • [ 881-57-2 ]
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Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2583 - 2591
  • 12
  • [ 69048-79-9 ]
  • [ 6451-86-1 ]
Reference: [1] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2583 - 2591
  • 13
  • [ 120-57-0 ]
  • [ 6451-86-1 ]
Reference: [1] Patent: WO2016/29214, 2016, A1
  • 14
  • [ 100-51-6 ]
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Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1067 - 1076
  • 15
  • [ 108-95-2 ]
  • [ 6451-86-1 ]
Reference: [1] Heterocycles, 1990, vol. 31, # 6, p. 1067 - 1076
  • 16
  • [ 2973-59-3 ]
  • [ 6451-86-1 ]
Reference: [1] Patent: WO2006/72818, 2006, A2. Location in patent: Page/Page column 18
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