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[ CAS No. 2830-53-7 ]

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Chemical Structure| 2830-53-7
Chemical Structure| 2830-53-7
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CAS No. :2830-53-7 MDL No. :MFCD09753753
Formula : C14H13BrO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :277.16 g/mol Pubchem ID :-
Synonyms :

Safety of [ 2830-53-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 2830-53-7 ]

  • Downstream synthetic route of [ 2830-53-7 ]

[ 2830-53-7 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 6627-55-0 ]
  • [ 100-44-7 ]
  • [ 2830-53-7 ]
YieldReaction ConditionsOperation in experiment
72% With potassium carbonate In acetonitrile Heating;
With potassium carbonate In N,N-dimethyl-formamide
With potassium carbonate
  • 2
  • [ 2830-53-7 ]
  • [ 115-19-5 ]
  • [ 163400-27-9 ]
YieldReaction ConditionsOperation in experiment
69% With copper(l) iodide; triphenylphosphine; palladium dichloride In triethylamine; N,N-dimethyl-formamide
  • 3
  • [ 2830-53-7 ]
  • [ 155835-37-3 ]
  • [ 215929-27-4 ]
YieldReaction ConditionsOperation in experiment
61% Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With magnesium In tetrahydrofuran Stage #2: (4R)-3-(3-phenyl-2-(E)-propenoyl)-4-phenyl-2-oxazolidinone With copper(I) bromide dimethylsulfide complex In tetrahydrofuran diastereoselective reaction; 1 4.8. General procedure for conjugate 1,4-addition of arylmagnesium bromides to cinnamic acid derivatives 2a-l in the presence of Cu(I) catalysts General procedure: Grignard reagent, prepared from 1-benzyloxy-2-bromo-4-methylbenzene (0.68g, 2.4mmol) and magnesium turnings (0.12g) in dry THF (10mL), was added to a cooled (-50°C) suspension of CuBr (71mg, 0.3equiv) in dry THF (3mL), then the temperature was allowed raise to -25°C and solution of cinnamide 2 (1.6mmol) in dry THF (4mL) was added keeping the temperature below -20°C. After the addition was completed the temperature was allowed to rise to room temperature and stirred overnight. The reaction mixture was quenched with 10% NH4Cl (10mL) and mixture was evaporated to remove all of the organic solvent. The aqueous layer was then extracted with ethyl acetate (3×25mL), and washed with 30ml of 17% NH4OH and 50ml of brine and dried over Na2SO4. Concentration in vacuo gave a crude product, which was purified by chromatography or crystallized. 4.8.1 (R)-3-[(R)-3-(2-Benzyloxy-5-methylphenyl)-3-phenylpro-pionyl]-4-phenyl-oxazolidin-2-one 8a. This compound was obtained from 2a (0.25g, 0.85mmol) in 0.26g amount (yield 61%) after chromatography (PE/EtOAc, 1.2:1) and further recrystallization of ether. White crystals; mp 116-117°C (Et2O); [α]D22=-72 (c 1.0, CHCl3); de 100%; Found: C, 77.50; H, 5.83; N, 2.79. C32H29NO4 requires C, 78.19; H, 5.95; N, 2.85%; 1H NMR (200MHz, CDCl3) δ 2.26 (s, 3H, CH3), 3.62 (dd, J=6.5, 16.8Hz, 1H, PhCHCH2), 3.89 (dd, J=8.9, 16.8Hz, 1H, PhCHCH2), 4.16 (dd, J=3.5, 8.8Hz, 1H, PhCHCH2), 4.50 (t, J=8.7Hz, 1H, NCH), 4.92 (s, 2H, PhCH2O), 5.02 (dd, J=6.5, 8.8Hz, 1H, NCHCH2), 5.28 (dd, J=3.5, 8.6Hz, 1H, NCHCH2), 6.71 (d, J=8.3Hz, 1H, 3(A)-aromH), 6.93 (dd, J=2.1, 8.3Hz, 1H, 4(A)-aromH), 7.06 (d, J=2.1Hz, 1H, 6(A)-aromH), 7.08-7.34 (m, 15H, aromH). 13C NMR (75MHz, CDCl3) δ 20.9, 40.0, 40.1, 57.7, 70.0, 70.2, 112.2, 125.7, 126.2, 127.4, 127.7, 127.9, 128.3, 128.4, 128.5, 128.6, 128.7, 129.2, 130.0, 132.0, 137.4, 139.1, 143.5, 153.9, 171.1.
With copper(I) bromide dimethylsulfide complex; dimethylsulfide; magnesium 1) THF, reflux, 15 min; 2) THF, -50 deg C, 3 min; 3) THF, 10 deg C, 2 h; Yield given. Multistep reaction;
  • 4
  • [ 100-44-7 ]
  • [ 2830-53-7 ]
  • 2-benzyl-6-bromo-4-methyl-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene
  • 5
  • [ 2830-53-7 ]
  • [ 220223-05-2 ]
YieldReaction ConditionsOperation in experiment
74% Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane at -78℃; for 1h; Stage #2: With sulfur dioxide In diethyl ether; hexane at -78 - 20℃; for 1.25h; Stage #3: With N-chloro-succinimide; sodium phosphate In water; ethyl acetate for 1h; ice-cooling;
  • 6
  • [ 2830-53-7 ]
  • [ 109588-48-9 ]
  • [ 834-25-3 ]
YieldReaction ConditionsOperation in experiment
1: 56% 2: 13% With 2,2'-azobis(isobutyronitrile); 1,1,2,2-tetraphenyldisilane In m-xylene for 22h; Heating;
1: 42% 2: 10% With azobis(2-cyanobutane); tri-n-butyl-tin hydride In cyclohexane Heating;
  • 7
  • [ 6627-55-0 ]
  • [ 100-39-0 ]
  • [ 2830-53-7 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone for 20h; Heating;
97% With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 11h; Synthesis of 1-(benzyloxy)-2-bromo-4-methylbenzene 2b To a stirred solution of the 2-bromo-4-methylphenol (0.5 g, 2.67 mmol, 1.0 equiv.),benzyl bromide (0.595 g, 3.48 mmol, 1.3 equiv.), and K2CO3 (0.739 g, 5.35 mmol, 2.0equiv.) in DMF (5 mL) was added at room temperature, then the reaction system wasstirred at 90 C. After 11 h, the reaction was completed by thin-layer chromatography(TLC). The mixture was diluted with EtOAc (12 mL), washed with saturated brine (10mL × 2). The organic layer was dried over anhydrous Na2SO4 and concentrated. Theresidue was purified by column chromatography on silica gel (200-300 m) with EtOAc/petroleum ether (v/v, 1:10) as the eluent to give the product 2b (716 mg, 97%, whitesolid).
91% With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide
90% With potassium carbonate In acetone for 4h; Reflux; 1.A To a solution of 2-bromo-4-methylphenol 32a (5 g, 26.7 mmol) in acetone (60 mL) was added K2CO3 (11 g, 80 mmol) followed by benzyl bromide (3.8 mL, 32 mmol). The mixture was heated to reflux for 4 hours, then was cooled to room temperature. Solid was removed via filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (5% EtO Ac/heptane) to give 6.7 g of Ha as a white semi-solid (yield 90%).
82% With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h; Inert atmosphere;
77% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 12h; 14.1 (1) Synthesis of 1-Benzyloxy-2-bromo-4-methylbenzene To a solution of 2-bromo-4-methylphenol (1.5 g, 8.0 mmol) in N,N-dimethylformamide (40 mL), potassium carbonate (1.32 g, 9.6 mmol) was added and furthermore benzyl bromide (1.05 mL, 8.8 mmol) was added thereto. The mixture solution was stirred at room temperature for 12 hours, and then water was added thereto and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution and dried (anhydrous magnesium sulfate), and then the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution= ethyl acetate: n-hexane (1:4)] to obtain the title compound (1.72 g, 77%). 1H-NMR (CDCl3) δ: 2.30 (3H, s), 5.12 (2H, s), 6.82 (1H, d, J=8.4Hz), 6.99-7.03 (1H, m), 7.28-7.41 (4H, m), 7.45-7.48 (2H, m)
77% With potassium carbonate In acetone for 4h; Reflux; 1.1.1 Step 1: The preparation of 1-(benzyloxy)-2-bromo-4-methylbenzene (compound 1) To a solution of 2-bromo-4-methylphenol (SM1, 20 g, 0.107 mol) in acetone (240 ml) were added (bromomethyl)benzene (SM2, 15.2 ml, 21.95 g, 0.128 mol) and K2CO3 (44.3 g, 0.321 mol). The mixture was heated to reflux for 4 hours, and was cooled to room temperature. The solution was poured into water (400 ml) and extracted with EA. The organic layer was washed with water for two times, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to obtain the crude product. The crude product was purified by column chromatography (PE: EA = 98: 2) to obtain the targetcompound 1 (23 g, 77.0 % yield).
36% Stage #1: 2-bromo-p-cresol With sodium hydride In tetrahydrofuran for 0.5h; Heating; Stage #2: benzyl bromide In tetrahydrofuran for 4h; Heating; Further stages.;
With potassium carbonate In acetone for 24h; Reflux;
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h;
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 12h; 3 1-(benzyloxy)-2-bromo-4-methylbenzene (3a) 1-(benzyloxy)-2-bromo-4-methylbenzene (3a) To a mixture of 2-bromo-4-methylphenol (5.0 g, 27 mmol) and K2CO3 (7.4 g, 53 mmol) in DMF (20 mL) was added benzyl bromide (3.5 mL, 29 mmol) at ambient temperature. It was stirred at 70° C., for 12 h. The mixture was poured into water (50 mL), extracted with EtOAc (150 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (10:1) to give the title compound (3a).
With tetra-(n-butyl)ammonium iodide; potassium carbonate In acetonitrile at 65℃; 1-(benzyloxy)-2-bromo-4-methylbenzene 2-bromocresol (12.9 g, 68.9 mmol), benzyl bromide (9.0 mL, 75.8 mmol), potassium carbonate (28.5 g, 206 mmol), and TBAI (approx. 100 mg) were heated overnight at 65°C in acetonitrile. Once cool, the mixture was filtered and concentrated under reduced pressure. The benzylated product was used withoutfurther purification.

Reference: [1]Soegel, Sebastian; Tokunaga, Norihito; Sasaki, Keigo; Okamoto, Kazuhiro; Hayashi, Tamio [Organic Letters, 2008, vol. 10, # 4, p. 589 - 592]
[2]Hu, Nvdan; Kong, Wenlong; Li, Shengkun; Song, Baoan; Wang, Xia [European Journal of Medicinal Chemistry, 2022, vol. 227]
[3]Vyvyan, James R.; Loitz, Celeste; Looper, Ryan E.; Mattingly, Cheryl S.; Peterson, Emily A.; Staben, Steven T. [Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2461 - 2468]
[4]Current Patent Assignee: CONCERT PHARMACEUTICALS INC - WO2009/126844, 2009, A2 Location in patent: Page/Page column 25
[5]Mangas-Sanchez, Juan; Busto, Eduardo; Gotor-Fernandez, Vicente; Gotor, Vicente [Organic Letters, 2010, vol. 12, # 15, p. 3498 - 3501]
[6]Current Patent Assignee: Chugai Pharmaceutical (in: Roche); ROCHE HOLDING AG - EP1783110, 2007, A1 Location in patent: Page/Page column 40
[7]Current Patent Assignee: HANGZHOU REX PHARMACEUTICAL - EP3476848, 2019, A1 Location in patent: Paragraph 0047-0048
[8]Bowman, Russell; Mann, Emma; Parr, Jonathan [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 17, p. 2991 - 2999]
[9]Mondragón, Alexander; Monsalvo, Iván; Regla, Ignacio; Castillo, Ivan [Tetrahedron Letters, 2010, vol. 51, # 4, p. 767 - 770]
[10]Location in patent: scheme or table Mangas-Sanchez, Juan; Busto, Eduardo; Gotor-Fernandez, Vicente; Gotor, Vicente [Organic Letters, 2011, vol. 13, # 20, p. 5711 - 5712]
[11]Current Patent Assignee: SHANGHAI FOSUN PHARMACEUTICAL (GROUP) CO., LTD.; Shanghai Institute of Materia Medica (in: CAS); CHINESE ACADEMY OF SCIENCES - US2014/128387, 2014, A1 Location in patent: Paragraph 0650; 0651
[12]Current Patent Assignee: EXXON MOBIL CORP - WO2019/27572, 2019, A1 Location in patent: Paragraph 00150
  • 8
  • [ 93-51-6 ]
  • [ 2830-53-7 ]
  • 2-benzyloxy-2'-methoxy-4',5'-dimethyldiphenyl ether [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With pyridine; copper(I) trifluoromethanesolfonate toluene complex; caesium carbonate at 110℃; for 24h;
  • 9
  • [ 2830-53-7 ]
  • [ 180303-11-1 ]
  • 1-Benzyloxy-4-methyl-2-(5-methyl-1-methylene-hex-4-enyl)-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1.16667h; Stage #2: With zinc(II) chloride In tetrahydrofuran; diethyl ether; pentane at -78 - 20℃; Stage #3: Trifluoro-methanesulfonic acid 5-methyl-1-methylene-hex-4-enyl ester In tetrahydrofuran; diethyl ether; pentane for 24h; Heating;
  • 10
  • [ 3054-95-3 ]
  • [ 2830-53-7 ]
  • (E)-3-(2-(benzyloxy)-5-methylphenyl)acrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With palladium diacetate; potassium chloride; potassium carbonate In N,N-dimethyl-formamide at 90℃; for 2.5h;
  • 11
  • [ 540-88-5 ]
  • [ 2830-53-7 ]
  • cis-3,5-dimethyl-3-hydroxy-2-phenyl-2,3-dihydrobenzo[b]furan [ No CAS ]
  • trans-3,5-dimethyl-3-hydroxy-2-phenyl-2,3-dihydrobenzo[b]furan [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 43% 2: 19% Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -25℃; Stage #2: acetic acid tert-butyl ester In tetrahydrofuran; pentane at -78 - 20℃;
  • 12
  • [ 540-88-5 ]
  • [ 2830-53-7 ]
  • [ 58110-77-3 ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78 - -25℃; Stage #2: acetic acid tert-butyl ester In tetrahydrofuran; pentane at -78 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water; pentane at 20℃;
  • 13
  • [ 4606-07-9 ]
  • [ 2830-53-7 ]
  • 3-cyclopropyl-5-methyl-2-phenylbenzo[b]furan [ No CAS ]
  • 14
  • [ 2830-53-7 ]
  • [ 33513-42-7 ]
  • [ 53389-98-3 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1-(benzyloxy)-2-bromo-4-methylbenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Further stages.;
  • 15
  • [ 2830-53-7 ]
  • [ 863970-29-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 41 percent / Pd(OAc)2; K2CO3; KCl / n-Bu4NOAc / dimethylformamide / 2.5 h / 90 °C 2: [Rh(C2H4)2Cl]2; chiral substituted bicyclo[2.2.2]octa-2,5-diene; aq. KOH / methanol / 1.25 h / 50 °C
  • 16
  • [ 2830-53-7 ]
  • (S)-3-(2-(benzyloxy)-5-methylphenyl)-3-phenylpropanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 41 percent / Pd(OAc)2; K2CO3; KCl / n-Bu4NOAc / dimethylformamide / 2.5 h / 90 °C 2: [Rh(C2H4)2Cl]2; chiral substituted bicyclo[2.2.2]octa-2,5-diene; aq. KOH / methanol / 1.25 h / 50 °C
  • 17
  • [ 2830-53-7 ]
  • 2-(1,5-dimethyl-hex-4-enyl)-1-hydroxy-4-methyl-benzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: tert-butyllithium / tetrahydrofuran; pentane / 1.17 h / -78 °C 1.2: zinc chloride / tetrahydrofuran; pentane; diethyl ether / -78 - 20 °C 1.3: Pd(PPh3)4 / tetrahydrofuran; pentane; diethyl ether / 24 h / Heating 2.1: 0.920 g / lithium; ammonia / diethyl ether / 1.5 h / cooling
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