Home Cart 0 Sign in  
X

[ CAS No. 73219-89-3 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 73219-89-3
Chemical Structure| 73219-89-3
Chemical Structure| 73219-89-3
Structure of 73219-89-3 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Bulk Inquiry Add To Cart

Quality Control of [ 73219-89-3 ]

Related Doc. of [ 73219-89-3 ]

Alternatived Products of [ 73219-89-3 ]

Product Details of [ 73219-89-3 ]

CAS No. :73219-89-3 MDL No. :MFCD00052933
Formula : C9H9BrO4 Boiling Point : -
Linear Structure Formula :- InChI Key :CUQANLQRQJHIQE-UHFFFAOYSA-N
M.W :261.07 Pubchem ID :2774744
Synonyms :

Safety of [ 73219-89-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 73219-89-3 ]

* 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 [ 73219-89-3 ]

[ 73219-89-3 ] Synthesis Path-Downstream   1~51

  • 1
  • [ 1466-76-8 ]
  • [ 73219-89-3 ]
YieldReaction ConditionsOperation in experiment
97% With bromine In acetic acid for 1.5h;
94% With sodium hydroxide; N-Bromosuccinimide for 5h; Ambient temperature;
85% With bromine In 1,4-dioxane; chloroform for 2h; Ambient temperature;
80% With bromine In chloroform at 0℃; for 1.5h;
With dioxane*Br2
With bromine In 1,4-dioxane; chloroform 1 Example 1. Example 1. 3-Bromo-2,6-dimethoxybenzoic acid A solution of 15 ml of bromine (0.3 mol) in 50 ml of chloroform is added dropwise while stirring and cooling in ice to 54.9 g (0.3 mol) of 2,6-dimethoxybenzoic acid in 150 ml of dioxan. The solution is left at room temperature overnight. The solvent is evaporated and the residue recrystallized from aqueous ethanol. Yield: 59.3 g, m.p. 144°-45° C.

  • 3
  • [ 73219-89-3 ]
  • [ 73219-92-8 ]
YieldReaction ConditionsOperation in experiment
80% With sulfuryl dichloride In chloroform 1.) RT, 12 h, 2.) reflux, 45 min;
  • 4
  • [ 73219-89-3 ]
  • [ 129295-49-4 ]
  • N-(1-Benzyl-4-methyl-[1,4]diazepan-6-yl)-3-bromo-2,6-dimethoxy-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 5h; Ambient temperature;
  • 5
  • [ 73219-89-3 ]
  • [ 22795-99-9 ]
  • [ 80125-14-0 ]
  • 6
  • [ 73219-89-3 ]
  • 1-bromo-3-iodo-2,4-dimethoxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With iodine; mercury(II) oxide In nitrobenzene at 160 - 165℃; for 2h;
  • 7
  • [ 100-42-5 ]
  • [ 73219-89-3 ]
  • 3-bromo-2,6-dimethoxystilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 0.5h;
48% With palladium(II) trifluoroacetate; 1-Adamantanecarboxylic acid; p-benzoquinone In 1,4-dioxane; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; optical yield given as %de; regioselective reaction;
  • 8
  • [ 930-68-7 ]
  • [ 73219-89-3 ]
  • 3-(3-bromo-2,6-dimethoxyphenyl)-2-cyclohexen-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With air; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 2h;
  • 9
  • [ 73219-89-3 ]
  • [ 586392-15-6 ]
YieldReaction ConditionsOperation in experiment
77% With borane-THF In tetrahydrofuran for 12h; Heating;
  • 10
  • [ 696-62-8 ]
  • [ 73219-89-3 ]
  • 3-bromo-2,4',6-trimethoxybiphenyl [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With triphenyl-arsane; silver carbonate In dimethyl sulfoxide at 150℃; for 6h;
  • 11
  • [ 73219-89-3 ]
  • N-{4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl}-3-bromo-6-hydroxy-2-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2, DMF / toluene / 2 h / 65 °C 2: 1.45 g / Et3N / CHCl3 / 0.5 h / Heating 3: 0.18 g / 1 N etheral HCl, BBr3 / CH2Cl2 / 0.5 h / Ambient temperature
  • 12
  • [ 73219-89-3 ]
  • N-{4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl}-3-bromo-2-hydroxy-6-methoxybenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2, DMF / toluene / 2 h / 65 °C 2: 1.45 g / Et3N / CHCl3 / 0.5 h / Heating 3: 2.06 g / 1 N etheral HCl, BBr3 / CH2Cl2 / 0.5 h / Ambient temperature
  • 13
  • [ 73219-89-3 ]
  • N-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-3-bromo-2,6-dimethoxy-benzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2, DMF / toluene / 2 h / 65 °C 2: 1.45 g / Et3N / CHCl3 / 0.5 h / Heating
  • 14
  • [ 73219-89-3 ]
  • [ 96947-79-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2, DMF / toluene / 1 h / 65 °C 2: 50 percent / CHCl3 / 0.5 h / 25 °C 3: 50 percent / 3N HCl, BBr3 / CH2Cl2 / 30 h / 20 °C
  • 15
  • [ 73219-89-3 ]
  • [ 96947-80-7 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: SOCl2, DMF / toluene / 1 h / 65 °C 2: 50 percent / CHCl3 / 0.5 h / 25 °C 3: 20 percent / 3N HCl, BBr3 / CH2Cl2 / 30 h / 20 °C
  • 16
  • [ 73219-89-3 ]
  • [ 84225-93-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2, DMF / toluene / 1 h / 65 °C 2: 50 percent / CHCl3 / 0.5 h / 25 °C
  • 17
  • [ 73219-89-3 ]
  • [ 82935-51-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / 0.5 h / Heating 2: Et3N / CHCl3 / Ambient temperature
  • 18
  • [ 73219-89-3 ]
  • [ 80125-14-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: SOCl2 / 0.5 h / Heating 2: 10N aq. NaOH / CHCl3 / 0.17 h / Heating
  • 19
  • [ 73219-89-3 ]
  • [ 89653-83-8 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 80 percent / SO2Cl2 / CHCl3 / 1.) RT, 12 h, 2.) reflux, 45 min 2: SOCl2 / 1 h / Heating
  • 20
  • [ 73219-89-3 ]
  • [ 84225-93-4 ]
YieldReaction ConditionsOperation in experiment
79% 10 (-)-N-n-propyl-2-(3-bromo-2,6 -dimethoxybenzamidomethyl)pyrrolidine Example 10 (-)-N-n-propyl-2-(3-bromo-2,6 -dimethoxybenzamidomethyl)pyrrolidine The title compound was prepared from 3-bromo-2,6-dimethoxybenzoic acid via the acylchloride and (-)-1-n-propyl-2-(aminomethyl)pyrrolidine in the same manner as described in Example 8. Yield 79%. M.p. 103°-104° C. [α]D20 =-85.4° (c=0.5; CHCl3).
  • 21
  • [ 26116-12-1 ]
  • [ 60-29-7 ]
  • [ 73219-89-3 ]
  • [ 73219-94-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride In toluene; butanone 7 Example 7. Example 7. N-Ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride 30 ml of thionyl chloride is added to 17.6 g (0.067 mol) of 3-bromo-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 9.23 g (0.072 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of methyl ethyl ketone. After stirring for 30 minutes at room temperature 150 ml of ethyl ether is added. The obtained precipitate is filtered off, washed with ether and recrystallized twice from ethanol-isopropyl ether. Yield: 21.0 g, m.p. 182°-84° C. (first recrystallization). m.p. 184°-85° C. (second recrystallization).
  • 22
  • (+)-2-(aminomethyl)-1-ethyl-pyrrolidine d-tartrate [ No CAS ]
  • [ 73219-89-3 ]
  • [ 73219-94-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine In water 15 Example 15. Example 15. N-Ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl) pyrrolidine hydrochloride Using the same method as for compound in Example 14, except of the addition of triethylamine, this compound was prepared from 8.4 g (0.032 mol) of 3-bromo-2,6-dimethoxybenzoic acid, 20 ml of thionyl chloride and 9.0 g (0.032 mol) of (+)-2-(aminomethyl)-1-ethylpyrrolidine d-tartrate. Yield: 7.5 g, m.p. 166°-68° C., [α]D20° =10.7° (0.5% in water).
  • 23
  • [ 73219-89-3 ]
  • [ 73219-94-0 ]
YieldReaction ConditionsOperation in experiment
With thionyl chloride; triethylamine In toluene 14 Example 14. Example 14. N-Ethyl-2-(3-bromo-2,6-dimethoxybenzamidomethyl) pyrrolidine hydrochloride 23.8 g (0.09 mol) of 3-bromo-2,6-dimethoxybenzoic acid is heated with 35 ml of thionyl chloride on a steam bath for 30 minutes. After the addition of toluene the excess thionyl chloride is evaporated at reduced pressure. To the residue is added dropwise while stirring a mixture of 12.6 g (0.09 mol) of triethylamine and a chloroform extract prepared as follows: 100 ml of 30% sodium hydroxide solution is added to 25.0 g (0.09 mol) of (-)-2-(aminomethyl)-1-ethylpyrrolidine 1-tartrate.
  • 24
  • [ 73219-89-3 ]
  • [ 66003-76-7 ]
  • [ 1039364-42-5 ]
YieldReaction ConditionsOperation in experiment
67% With silver carbonate; bis[2-(diphenylphosphino)phenyl] ether; palladium dichloride In dimethyl sulfoxide at 150℃; for 1h;
  • 25
  • [ 695-12-5 ]
  • [ 73219-89-3 ]
  • [ 1159205-74-9 ]
  • [ 1159205-73-8 ]
  • [ 1159205-75-0 ]
YieldReaction ConditionsOperation in experiment
With palladium(II) trifluoroacetate; 1-Adamantanecarboxylic acid; p-benzoquinone In 1,4-dioxane; dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 1h; Inert atmosphere; optical yield given as %de; regioselective reaction;
  • 26
  • [ 79-24-3 ]
  • [ 73219-89-3 ]
  • [ 1242462-16-3 ]
YieldReaction ConditionsOperation in experiment
52% With palladium(II) trifluoroacetate; dimethyl sulfoxide; silver carbonate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;
  • 27
  • [ 73219-89-3 ]
  • [ 106-51-4 ]
  • [ 1258167-99-5 ]
YieldReaction ConditionsOperation in experiment
36% With palladium diacetate; dimethyl sulfoxide; silver carbonate In N,N-dimethyl-formamide at 120℃; for 3h;
  • 28
  • [ 73219-89-3 ]
  • [ 292638-85-8 ]
  • [ 1253180-88-9 ]
YieldReaction ConditionsOperation in experiment
85% With oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 120℃; for 10h; optical yield given as %de; diastereoselective reaction;
  • 29
  • [ 73219-89-3 ]
  • [ 75-05-8 ]
  • [ 1259663-52-9 ]
YieldReaction ConditionsOperation in experiment
61% With palladium(II) trifluoroacetate; 6-methyl-2,2'-bipyridine In water at 130℃; for 1h; Microwave irradiation;
  • 30
  • [ 73219-89-3 ]
  • [ 106-95-6 ]
  • [ 1269809-26-8 ]
YieldReaction ConditionsOperation in experiment
60% With copper(I) oxide; palladium diacetate; dimethyl sulfoxide; silver carbonate In toluene at 110℃; for 2h; chemoselective reaction;
  • 31
  • [ 73219-89-3 ]
  • [ 149104-90-5 ]
  • [ 1262967-35-0 ]
YieldReaction ConditionsOperation in experiment
66% With copper(II) bis(trifluoromethanesulfonate); silver carbonate In dimethyl sulfoxide at 120℃; for 2h; Sealed vial;
  • 32
  • [ 73219-89-3 ]
  • [ 89337-62-2 ]
  • [ 1262097-86-8 ]
  • [ 1262097-87-9 ]
YieldReaction ConditionsOperation in experiment
1: 11% 2: 26% With N,N-diphenylaminobenzene; oxygen; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 90℃; for 24h; Molecular sieve; optical yield given as %de;
  • 33
  • [ 73219-89-3 ]
  • [ 2873-29-2 ]
  • [ 1323988-61-9 ]
YieldReaction ConditionsOperation in experiment
43% With palladium diacetate; triphenylphosphine; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere; stereoselective reaction;
  • 34
  • [ 73219-89-3 ]
  • [ 4098-06-0 ]
  • [ 1323988-65-3 ]
YieldReaction ConditionsOperation in experiment
47% With palladium diacetate; triphenylphosphine; silver carbonate In dimethyl sulfoxide; N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere; stereoselective reaction;
  • 35
  • [ 96-43-5 ]
  • [ 73219-89-3 ]
  • [ 1356488-33-9 ]
YieldReaction ConditionsOperation in experiment
40% With palladium(II) trifluoroacetate; silver carbonate; tricyclohexylphosphine In 1,2-dimethoxyethane; dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;
  • 36
  • [ 73219-89-3 ]
  • [ 131667-57-7 ]
  • [ 1421692-68-3 ]
YieldReaction ConditionsOperation in experiment
16% With silver (II) carbonate; palladium diacetate; propionic acid; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 24h;
  • 37
  • [ 111-34-2 ]
  • [ 73219-89-3 ]
  • C14H19BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
41% With palladium(II) trifluoroacetate; p-benzoquinone; 6-methyl-2,2'-bipyridine In N,N-dimethyl-formamide at 120℃; for 24h; regioselective reaction;
  • 38
  • [ 3195-78-6 ]
  • [ 73219-89-3 ]
  • N-(1-(3-bromo-2,6-dimethoxyphenyl)vinyl)-N-methylacetamide [ No CAS ]
  • 39
  • [ 88-12-0 ]
  • [ 73219-89-3 ]
  • 1-(1-(3-bromo-2,6-dimethoxyphenyl)vinyl)pyrrolidin-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% With palladium(II) trifluoroacetate; p-benzoquinone; 6-methyl-2,2'-bipyridine In N,N-dimethyl-formamide at 120℃; for 24h; regioselective reaction;
  • 40
  • [ 2235-00-9 ]
  • [ 73219-89-3 ]
  • 1-(1-(3-bromo-2,6-dimethoxyphenyl)vinyl)azepan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
25% With palladium(II) trifluoroacetate; p-benzoquinone; 6-methyl-2,2'-bipyridine In N,N-dimethyl-formamide at 120℃; for 24h; regioselective reaction;
  • 41
  • [ 7748-07-4 ]
  • [ 73219-89-3 ]
  • C13H17BrO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With palladium(II) trifluoroacetate; p-benzoquinone; 6-methyl-2,2'-bipyridine In N,N-dimethyl-formamide at 120℃; for 24h; regioselective reaction;
  • 42
  • [ 617-90-3 ]
  • [ 73219-89-3 ]
  • [ 206348-24-5 ]
YieldReaction ConditionsOperation in experiment
50% With Pd(2+)*2C5F9O2(1-); trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 130℃; for 1h; Microwave irradiation; Procedure for the synthesis of ketone 3q, 3y, 3ad,Table 3 conditions [b] General procedure: A 2 mL microwave vialwas charged with 6-methyl-2,2'-bipyridine (16.3 mg, 0.096 mmol), Pd(O2CCF3)2(26.6 mg, 0.08 mmol) and 500 µL THF. After stirring at room temperature for 5minutes, 3-bromo-2,6-dimethoxybenzoic acid (261.1 mg, 1 mmol), nitrile (5mmol), water (50 µL) and TFA (77 µL, 1 mmol) were added and the mixture heated inthe microwave for 1 hour at 130 °C. Themixture was diluted with DCM (15 mL) and 0.1 M NaOH (15 mL), the phases wereseparated and extracted with DCM (2 ×15 mL), dried with Na2SO4, filtered and concentratedunder reduced pressure. Purification by flash chromatography afforded ketones 3q,3y or 3ad in the yields statedin Table 3.
  • 43
  • [ 100-54-9 ]
  • [ 73219-89-3 ]
  • [ 1600514-96-2 ]
YieldReaction ConditionsOperation in experiment
19% With Pd(2+)*2C5F9O2(1-); trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 130℃; for 1h; Microwave irradiation; Procedure for the synthesis of ketone 3q, 3y, 3ad,Table 3 conditions [b] General procedure: A 2 mL microwave vialwas charged with 6-methyl-2,2'-bipyridine (16.3 mg, 0.096 mmol), Pd(O2CCF3)2(26.6 mg, 0.08 mmol) and 500 µL THF. After stirring at room temperature for 5minutes, 3-bromo-2,6-dimethoxybenzoic acid (261.1 mg, 1 mmol), nitrile (5mmol), water (50 µL) and TFA (77 µL, 1 mmol) were added and the mixture heated inthe microwave for 1 hour at 130 °C. Themixture was diluted with DCM (15 mL) and 0.1 M NaOH (15 mL), the phases wereseparated and extracted with DCM (2 ×15 mL), dried with Na2SO4, filtered and concentratedunder reduced pressure. Purification by flash chromatography afforded ketones 3q,3y or 3ad in the yields statedin Table 3.
  • 44
  • [ 73219-89-3 ]
  • [ 140-29-4 ]
  • [ 1600514-88-2 ]
YieldReaction ConditionsOperation in experiment
68% With Pd(2+)*2C5F9O2(1-); trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 130℃; for 1h; Microwave irradiation; Procedure for the synthesis of ketone 3q, 3y, 3ad,Table 3 conditions [b] General procedure: A 2 mL microwave vialwas charged with 6-methyl-2,2'-bipyridine (16.3 mg, 0.096 mmol), Pd(O2CCF3)2(26.6 mg, 0.08 mmol) and 500 µL THF. After stirring at room temperature for 5minutes, 3-bromo-2,6-dimethoxybenzoic acid (261.1 mg, 1 mmol), nitrile (5mmol), water (50 µL) and TFA (77 µL, 1 mmol) were added and the mixture heated inthe microwave for 1 hour at 130 °C. Themixture was diluted with DCM (15 mL) and 0.1 M NaOH (15 mL), the phases wereseparated and extracted with DCM (2 ×15 mL), dried with Na2SO4, filtered and concentratedunder reduced pressure. Purification by flash chromatography afforded ketones 3q,3y or 3ad in the yields statedin Table 3.
  • 45
  • [ 16532-79-9 ]
  • [ 73219-89-3 ]
  • [ 1600514-91-7 ]
YieldReaction ConditionsOperation in experiment
73% With Pd(2+)*2C5F9O2(1-); trifluoroacetic acid; 6-methyl-2,2'-bipyridine In tetrahydrofuran; water at 130℃; for 1h; Microwave irradiation; Procedure for the synthesis of ketone 3u, 3yand 3ad, Table 3 conditions [d] General procedure: A 2 mL microwave vialwas charged with 6-methyl-2,2'-bipyridine (16.3 mg, 0.096 mmol), Pd(O2CCF3)2(26.6 mg, 0.08 mmol) and 500 µL THF. After stirring at room temperature for 5minutes, 3-bromo-2,6-dimethoxybenzoic acid (522.2 mg, 2 mmol), nitrile (1mmol), water (50 µL) and TFA (77 µL, 1 mmol) were added and the mixture heatedin the microwave for 1 hour at 130 °C. The mixture was diluted with DCM (15 mL)and 0.1 M NaOH (15 mL), the phases were separated and extracted with DCM (2 ×15 mL), dried with Na2SO4, filtered and concentrated under reduced pressure. Purificationby flash chromatography afforded ketones 3u,3y or 3ad in the yields stated in Table 3.
  • 46
  • [ 14371-10-9 ]
  • [ 73219-89-3 ]
  • (Z)-3-(3-bromo-2,6-dimethoxyphenyl)-3-phenylacrylaldehyde [ No CAS ]
  • (E)-3-(3-bromo-2,6-dimethoxyphenyl)-3-phenylacrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
29% With silver(I) iodate; Tri(p-tolyl)phosphine; palladium dichloride In N,N-dimethyl-formamide at 120℃; for 1h; Sealed tube; Overall yield = 37 %Spectr.; stereoselective reaction;
17% With silver(I) iodate; Tri(p-tolyl)phosphine; palladium dichloride In tetrahydrofuran at 120℃; for 22h; Sealed tube; Overall yield = 38 %Spectr.; stereoselective reaction;
  • 47
  • 4-methoxy-trans-cinnamaldehyde [ No CAS ]
  • [ 73219-89-3 ]
  • (Z)-3-(3-bromo-2,6-dimethoxyphenyl)-3-(4-methoxyphenyl)acrylaldehyde [ No CAS ]
  • (E)-3-(3-bromo-2,6-dimethoxyphenyl)-3-(4-methoxyphenyl)acrylaldehyde [ No CAS ]
YieldReaction ConditionsOperation in experiment
21% With silver(I) iodate; Tri(p-tolyl)phosphine; palladium dichloride In N,N-dimethyl-formamide at 120℃; for 1h; Sealed tube; Overall yield = 30 %Spectr.; stereoselective reaction;
19% With silver(I) iodate; Tri(p-tolyl)phosphine; palladium dichloride In tetrahydrofuran at 120℃; for 17h; Sealed tube; Overall yield = 32 %Spectr.; stereoselective reaction;
  • 48
  • [ 73219-89-3 ]
  • [ 100-39-0 ]
  • benzyl 3-bromo-2,6-dimethoxybenzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
12 g With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 2h; 46.i (i) Benzyl 3-bromo-2,6-dimethoxybenzoate (i) Benzyl 3-bromo-2,6-dimethoxybenzoate Benzyl bromide (5 mL, 42.0 mmol) was added to a thick suspension of 3-bromo-2,6- dimethoxybenzoic acid (9.4 g, 36.0 mmol) and K2C03 (20 g, 145 mmol) in DMF (300 mL). The mixture was heated at 70°C (block temperature 55°C internal) for 2h. The reaction mixture was concentrated in vacuo to circa 20 mL then partitioned between diethyl ether (500 mL) and 20%w/w NaCI soln. (250 mL). The organics were separated, and washed successively with a 10%vol/vol solution of 880 ammonia in water (250 mL) 1 N HCI (250 mL) and sat. NaHCOs (250 mL). The organics were separated, dried (MgSCU), filtered and evaporated to afford the sub-title compound (12 g). 1 H NMR (400 MHz, DMSO-d6) δ 7.68 (d, 1 H), 7.52 - 7.28 (m, 5H), 6.90 (d, 1 H), 5.35 (s, 2H), 3.79 (s, 3H), 3.70 (s, 3H). LCMS m/z 351/353 (M+H)+ (ES+); BP 373/375 (M+Na)+ (ES+)
  • 49
  • [ 73219-89-3 ]
  • [ 115269-99-3 ]
  • (E)-N,N-bis(tert-butoxycarbonyl)-3-(3-bromo-2,6-dimethoxyphenyl)prop-2-en-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction; 4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.
  • 50
  • [ 7065-05-6 ]
  • [ 73219-89-3 ]
  • (E)-2-(4-(3-bromo-2,6-dimethoxyphenyl)but-3-en-2-yl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction; 4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.
  • 51
  • [ 2049-80-1 ]
  • [ 73219-89-3 ]
  • (E)-diethyl 2-(3-(3-bromo-2,6-dimethoxyphenyl)allyl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With palladium(II) trifluoroacetate; silver carbonate In tetrahydrofuran; dimethyl sulfoxide at 100℃; for 8h; Inert atmosphere; stereoselective reaction; 4.2. General procedure for the decarboxylative arylation of olefins with aryl carboxylic acids General procedure: To an oven-dried pressure tube were sequentially added aryl carboxylic acid 1 (0.2 mmol), olefin 2 (0.24 mmol), Pd(TFA)2 (3.33 mg, 5.0 mol%), Ag2CO3 (55.2 mg, 0.2 mmol), THF (2.0 mL) and DMSO (0.10 mL) under nitrogen at room temperature. After degassing three times, the reaction mixture was heated at 100 °C for 8 h, and then was cooled to room temperature. Water (20.0 mL)was added, and the mixture was extracted with ethyl acetate (3 5.0 mL). The combined organic layer was washed with brine, dried over anhydrious Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate) to give the pure target product.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 73219-89-3 ]

Aryls

Chemical Structure| 32246-20-1

[ 32246-20-1 ]

5-Bromo-2,4-dimethoxybenzoic acid

Similarity: 1.00

Chemical Structure| 98437-41-3

[ 98437-41-3 ]

5-Bromo-2-hydroxy-4-methoxybenzoic acid

Similarity: 1.00

Chemical Structure| 27703-53-3

[ 27703-53-3 ]

3,5-Dibromo-2,6-dihydroxy-4-methoxybenzoic acid

Similarity: 0.98

Chemical Structure| 73219-90-6

[ 73219-90-6 ]

3,5-Dibromo-2,6-dimethoxybenzoic acid

Similarity: 0.98

Chemical Structure| 84225-86-5

[ 84225-86-5 ]

3-Bromo-2-hydroxy-6-methoxybenzoic acid

Similarity: 0.98

Bromides

Chemical Structure| 32246-20-1

[ 32246-20-1 ]

5-Bromo-2,4-dimethoxybenzoic acid

Similarity: 1.00

Chemical Structure| 98437-41-3

[ 98437-41-3 ]

5-Bromo-2-hydroxy-4-methoxybenzoic acid

Similarity: 1.00

Chemical Structure| 27703-53-3

[ 27703-53-3 ]

3,5-Dibromo-2,6-dihydroxy-4-methoxybenzoic acid

Similarity: 0.98

Chemical Structure| 73219-90-6

[ 73219-90-6 ]

3,5-Dibromo-2,6-dimethoxybenzoic acid

Similarity: 0.98

Chemical Structure| 84225-86-5

[ 84225-86-5 ]

3-Bromo-2-hydroxy-6-methoxybenzoic acid

Similarity: 0.98

Ethers

Chemical Structure| 32246-20-1

[ 32246-20-1 ]

5-Bromo-2,4-dimethoxybenzoic acid

Similarity: 1.00

Chemical Structure| 98437-41-3

[ 98437-41-3 ]

5-Bromo-2-hydroxy-4-methoxybenzoic acid

Similarity: 1.00

Chemical Structure| 27703-53-3

[ 27703-53-3 ]

3,5-Dibromo-2,6-dihydroxy-4-methoxybenzoic acid

Similarity: 0.98

Chemical Structure| 73219-90-6

[ 73219-90-6 ]

3,5-Dibromo-2,6-dimethoxybenzoic acid

Similarity: 0.98

Chemical Structure| 84225-86-5

[ 84225-86-5 ]

3-Bromo-2-hydroxy-6-methoxybenzoic acid

Similarity: 0.98

Carboxylic Acids

Chemical Structure| 32246-20-1

[ 32246-20-1 ]

5-Bromo-2,4-dimethoxybenzoic acid

Similarity: 1.00

Chemical Structure| 98437-41-3

[ 98437-41-3 ]

5-Bromo-2-hydroxy-4-methoxybenzoic acid

Similarity: 1.00

Chemical Structure| 27703-53-3

[ 27703-53-3 ]

3,5-Dibromo-2,6-dihydroxy-4-methoxybenzoic acid

Similarity: 0.98

Chemical Structure| 73219-90-6

[ 73219-90-6 ]

3,5-Dibromo-2,6-dimethoxybenzoic acid

Similarity: 0.98

Chemical Structure| 84225-86-5

[ 84225-86-5 ]

3-Bromo-2-hydroxy-6-methoxybenzoic acid

Similarity: 0.98