[ CAS No. 1835-02-5 ]

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CAS No. :1835-02-5MDL No. :MFCD03425186
Formula :C10H11BrO3InChI Key :NUAIPKMBWNVQIM-UHFFFAOYSA-N
M.W :259.10Pubchem ID :270423
Boiling Point :326.5°C at 760 mmHg
Synonyms :

Computed Properties

TPSA : 35.5 H-Bond Acceptor Count : 3
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 4

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 1835-02-5 ] Synthesis Path-Upstream   1~9

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YieldReaction ConditionsOperation in experiment
83% With benzyltrimethylazanium tribroman-2-uide In methanol; dichloromethane for 16.00 h; To a stirred solution of 1 -(3,4-dimethoxyphenyl)ethanone (1 .0 g, 5.55 mmol) in dichloromethane (6 mL) and methanol (3 mL) was added benzyltrimethylammonium tribromide (2.16 g, 5.55 mmol). After16 h, the mixture was diluted with dichloromethane (80 mL) and water (40 mL), the organic layer wasseparated, and the water phase was extracted with dichloromethane (80 mL x 2). The combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated to give 2-bromo-1 -(3,4-dimethoxyphenyl)ethanone (1.20 g, 4.63 mmol, 83 percent) as a brown solid. 1H NMR (400 MHz, ODd3) O 7.63 (s, 1 H), 7.57 (d, J2.1 Hz, 1 H), 6.94 (d, J8.4 Hz, 1 H), 4.43 (s, 2H), 3.98 (d, J8.4 Hz, 6H).
78% With N-Bromosuccinimide; toluene-4-sulfonic acid In acetonitrile at 85℃; for 4.00 h; General procedure: A mixture of substituted arylethanones 14a-i (10 mmol), N-bromosuccinimide (1.4 g, 12 mmol) and p-toluenesulphonic acid (2.8 g, 15 mmol) in acetonitrile (50 mL) was stirred at 85 °C for 4 h. After completion of reaction (indicated by TLC), the reaction mass was allowed to reach ambient temperature and evaporated excess of acetonitrile under reduced pressure. The residue so obtained was mixed in water, extracted with ethyl acetate (2 × 50 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuuo. The crude product obtained was recrystallized from n-hexane to afford pure 1-aryl-2-bromoethanones 15a-i in 75-85percent yields.
73% With bromine In diethyl ether; chloroform at 0 - 20℃; for 2.50 h; Step 1. 2-Bromo-1-(3,4-dimethoxy-phenyl)-ethanone. To a 0° C. solution of 3,4-dimethoxyacetophenone (5.00 g, 27.8 mmol) in diethyl ether (200 mL) and CHCl3 (30 mL) was added, dropwise over 1.5 h, a solution of Br2 (1.45 mL, 27.8 mmol) in CHCl3 (30 mL). Once the addition was complete, the mixture was stirred for 1 h at 0° C., and then was allowed to warm to rt. The reaction mixture was concentrated and the residue chromatographed (CH2Cl2/hexanes) to give 5.23 g (73percent) of the ketone as a pale yellow solid. 1H NMR (DMSO-d6): 7.68 (dd, J=2.0, 8.4, 1H), 7.47 (d, J=2.0, 1H), 7.08 (d, J=8.5, 1H), 4.85 (s, 2H), 3.85 (s, 3H), 3.81 (s, 3H).
70% With bromine In chloroform at 20℃; for 3.00 h; To a stirred solution of 1-(3,4-Dimethoxy-phenyl)-ethanone (7) (20 g, 0.111 mol) in chloroform (200 mL) at RT added bromine solution (18.8 g, 0.111 mol) in chloroform 90 mL) over 1 h, reaction maintained at RT for 2 h, after completion of reaction by TLC, the reaction mixture quenched in to saturated sodium bicarbonate solution (300 mL) and extracted with chloroform (2 X 150 mL), organic layers combined and washed with DM water (300 mL) and dried over sodium sulfate and concentrated, co distilled with hexane (2 X 100 mL), charged methanol (50 mL) and stirred for 10 min, filtered solid (8) 20 g (70percent); mp 79-81° C; IR (KBr, Cm-1): 3570, 2779, 1684, 1266; Mass for C10H11BrO3 [M+1] 259.0; 1H NMR (400MHz, DMSO) (δ ppm): 3.84 (3H, s), 3.88 (3H, s), 4.21 (2H, s), 7.07 (1H, d, J = 8.4 Hz), 7.43 (1H, s), 7.71 (1H, dd, J1 = 1.46 Hz, J2 = 1.48 Hz); 13C NMR (100 MHz, DMSO) (δ ppm); 33.87, 55.91, 56.16, 111.1, 111.2, 124.1, 127.0, 149.0, 153.9, 190.5.
63.4% With copper(I) bromide In chloroform; ethyl acetate at 20 - 65℃; for 16.00 h; Compound 2(27.78 mmol, 5.00 g, 1 eq) was dissolved in 90 mL of chloroform / ethyl acetate (1: 1 by volume)In the mixed solution,Copper bromide (55.56 mmol, 12.41 g, 2 eq) was added with stirring at room temperature,Heated to 65 reflux 16 h,TLC monitors the progress of the reaction.After the reaction (the reaction liquid is blue-black,The bottom of a large number of white solid precipitation),Cooling continue stirring 0.5 h,Filter, add appropriate amount of methylene chloride to the residue to continue filtration,The combined filtrates,Dried to 6.21 g of crude product (blue black solid),The crude product was isolated and purified by silica gel column chromatography (200-300 mesh) (ethyl acetate-petroleum 0: 100 →2: 98 → 5: 95 → 10: 80 → 20: 80 → 30: 70)Finally, compound 3 (4.53 g) was obtained,Yellow-brown solid,Yield 63.4percent.
52.3% With pyridinium hydrobromide perbromide In ethanol; chloroform at 50℃; for 16.00 h; Step 12-bromo-1 -(3,4-dimethoxyphenyl)eth3,4-dimethoxyacetophenone (1 .00 g, 5.55 mmol) was dissolved in a 1 :1 mixture of ethanol and chloroform (60 ml_). Pyridinium tribromide (4.46 g, 13.9 mmol) was added and the mixture was stirred at 50°C for 16 h. The reaction was cooled to RT and solvents removed in vacuo to give a sticky orange solid, which was then dissolved in H20 (30 ml_), and organics extracted with EtOAc (3 x 20 mL) and washed with H20 (2 x 20 mL) and brine (20 mL). The organics were dried (MgS04), filtered and concentrated in vacuo to give an orange oil containing a mixture of mono- and di-bromated species (approx 1 :5 to 1 ratio). Flash chromatography (DCM isocratic) afforded the title compound as an off-white solid (752 mg, 2.90 mmol. 52.3percent). Spectroscopic data was consistent with that previously reported. Mpt: 62 °C [Lit. 67-70 °C]; Rf = 0.12 (DCM); IR (vmax/cm-\\ thin film): 2940 (C-H stretch), 1679 (C=0 stretch), 1585, 1512, 1465, 1418 (Aromatic C=C stretch), 1241 (C-O-C stretch); 1H NMR (500 MHz, CDCI3): δΗ = 3.93 (s, 3H, 9-H), 3.95 (s, 3H, 10-H), 4.40 (s, 2H, 1 -H), 6.90 (d, J = 8.4 Hz, 1 H, 5-H), 7.53 (d, J = 2.1 Hz, 1 H, 8-H), 7.60 (dd, J = 8.4, 2.1 Hz, 1 H, 4-H); 13C NMR (125 MHz, CDCI3): 5C = 30.5 (C-1 ), 56.1 (C-9), 56.2 (C-10), 1 10.2 (C-5), 1 10.9 (C-8), 123.9 (C-4), 127.1 (C- 3), 149.4 (C-7), 154.1 (C-6), 190.2 (C-2); LRMS m/z (El+): 260 [M(81Br)]+, 258 [M(79Br)]+, 165 [M-CH2Br]+; HRMS m/z (El+): Found 257.98872 [M(79Br)]+; Ci0HnO3Br requires 257.98861 .
49% With bromine In chloroform at 20℃; 3,4-Dimethoxyacetophenone (10 g, 55 mmol) in CHCl3 (100 mL) was stirred in a round-bottom flask, while Br2 (10.6 g, 66 mmol) was added drop-wise over 1 h; the mixture was then stirred then for 16 h at r.t. The solvent was then removed in vacuo to give an oil; addition of EtOH (40 mL) and cooling to -15 °C gave a cream-white precipitate that was filtered off, washed with EtOH (2 9 20 mL), and dried in vacuo. Yield = 7.0 g (49 percent). 1H NMR (300 MHz, CDCl3): δH = 3.95, 3.97 (OCH3, s, 3H each), 4.42 (CH2Br, s, 2H), 6.92 (Ar–H, d,1H, 3JHH = 8.7), 7.56 (Ar–H, s,1H),7.62(Ar–H, d, 1H, 3JHH = 8.4). 13C{1H} NMR (75 MHz, CDCl3): δC = 30.5 (CH2Br), 56.1, 56.2 (OCH3), 110.2, 110.9, 123.9 (CAr–H), 127.1 (CArC=O), 149.4, 154.1 (CAr–OCH3), 190.1 (C=O). ESI/MS+: 283 [M + Na]+. Anal. Calcd (Found) for C10H11O3Br: C, 46.36 (46.37); H, 4.28 (4.25).
71% With bromine In chloroform Preparation example 64
Synthesis of (E)-N-[2-(3,4-dimethoxyphenyl)-2-oxoethyl]-N-methyl-3-(3-pyridyl)-2-propenamide (compound 155)
250 mL of ether and 100 mL of chloroform were added to 14.65 g (81 mmol) of 3',4'-dimethoxyacetophenone and the mixture was stirred while cooling on ice.
4.1 mL of bromine was dissolved in 22 mL of chloroform, and added dropwise to the reaction mixture over 1 h.
After stirring the reaction mixture for 1 h at room temperature, the reaction mixture was washed with water, aqueous saturated sodium bicarbonate, and water in that order.
The organic phase was dried over magnesium sulfate and the solvent was then removed by vacuum evaporation.
The residue was purified by silica gel column chromatography (dichloromethane: ethyl acetate = 30:1) to obtain 14.90 g (71percent) of 2-bromo-1-(3,4-dimethoxyphenyl)ethanone.
1H-NMR (CDCl3)δ: 3.95 (3H, s), 3.97 (3H, s), 4.41 (2H, s), 6.91 (1H, d, J=8Hz), 7.55 (1H, d, J=2Hz), 7.62 (1H, dd, J=8Hz, 2Hz)

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