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HazMat fee for 500 gram (Estimated)
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Structure of 79996-99-9 * Storage: {[proInfo.prStorage]}
* 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.
With tetrabutylammomium bromide In ethyl acetate at 70℃; for 9 h;
Weigh 4-Bromo-1-methylnaphthalene3.3 g (10.2 mmol, 1.5 eq) of tetrabutylammonium bromide was added to 30 mL of ethyl acetate and the mixture was refluxed at 70 ° C for 9 hours. After TLC showed that the starting material was completely reacted, The reaction was stopped. After filtering, the filter cake was stirred at room temperature for 2 hours with 30 mL of ethyl acetate and filtered to give 1.60 g of 1-bromo-4- (bromomethyl) naphthalene as a pale yellow solid in a yield of 77.43percent.
73%
With N-Bromosuccinimide; dibenzoyl peroxide In hexane for 36 h; Reflux; Inert atmosphere
A suspension of 11 (35.37 g, 160 mmol), BPO (0.78 g, 3.2 mmol), and NBS (34.17 g, 192 mmol) in n-hexane (400 mL) was refluxed under N2 until the completion of reaction as indicated by TLC analysis (typically 36 h; once the reaction commenced, 0.78 g of BPO was added every 8 h until the reaction completed). The reaction mixture was cooled to room temperature while stirring, and the precipitates were collected via vacuum filtration. The precipitates were triturated successively with saturated aqueous NaHCO3 (500 mL x 2), water (800 mL x 2), and n-hexane (800 mL) to give rise to (4-bromonaphth-1-yl)methyl bromide 12. White solid; 35.04 g (73percent); m.p. 104.5–106 °C (literature value, 102–104 °C [44]). 1H-NMR (DMSO-d6, 400 MHz) δ: 8.20–8.26 (m, 2H), 7.85 (d, J = 7.6 Hz, 1H), 7.71–7.77 (m, 2H), 7.62 (d, J = 7.6 Hz, 1H), 5.21 (s, 2H).
500 g
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 70 - 78℃;
A 5 L four-necked flask was charged with 461.8 g of 4-bromo-1-methylnaphthalene (I)7.2kg of carbon tetrachloride,375.6 g of N-bromosuccinimide,20.5 g BP0,The temperature was raised to 70 to 78 ° C (preferably 77 ° C) and the reaction was refluxed overnight.Point plate,The reaction is complete.Cooled to room temperature,Filter,40 ° C spin dry solvent.Add 1200 g of ethanol,Heating up to 70 ° C Paul lh,Cooling to room temperature,Filter,Filter cake washed with ethanol,After draining,Dried at 35 ° C to give 500 g of 4-bromo-1-bromomethylnaphthalene (II)The two-step yield was 79percent (based on 1-methylnaphthalene).
Reference：
[1] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[2] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1387 - 1390
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[4] Patent: CN105906530, 2016, A, . Location in patent: Paragraph 0091; 0092; 0093; 0094; 0095
[5] Organic Letters, 2008, vol. 10, # 14, p. 3105 - 3108
[6] Molecules, 2016, vol. 21, # 11,
[7] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[8] MedChemComm, 2016, vol. 7, # 5, p. 900 - 905
[9] Angewandte Chemie - International Edition, 2006, vol. 45, # 32, p. 5311 - 5315
[10] Journal of the Chemical Society, 1927, p. 3104
[11] Journal of the American Chemical Society, 1954, vol. 76, p. 604
[12] Dyes and Pigments, 2011, vol. 88, # 1, p. 57 - 64
[13] Chemical Communications, 2016, vol. 52, # 9, p. 1949 - 1952
[14] Patent: CN106366018, 2017, A, . Location in patent: Paragraph 0038; 0039
[15] Patent: WO2017/147328, 2017, A1, . Location in patent: Paragraph 0377
[16] Patent: WO2010/79077, 2010, A1, . Location in patent: Page/Page column 34
4
[ 90-12-0 ]
[ 79996-99-9 ]
Reference：
[1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[2] Chemische Berichte, 1922, vol. 55, p. 1854
[3] Journal of the Chemical Society, 1927, p. 3104
[4] Patent: CN105906530, 2016, A,
[5] Patent: CN106366018, 2017, A,
5
[ 56052-26-7 ]
[ 79996-99-9 ]
Reference：
[1] Canadian Journal of Chemistry, 1981, vol. 59, p. 2629 - 2641
Reference：
[1] Chemische Berichte, 1922, vol. 55, p. 1854
13
[ 6627-78-7 ]
[ 7726-95-6 ]
[ 79996-99-9 ]
Reference：
[1] Journal of the Chemical Society, 1927, p. 3104
14
[ 75-15-0 ]
[ 7726-95-6 ]
[ 90-12-0 ]
[ 6627-78-7 ]
[ 79996-99-9 ]
Reference：
[1] Chemische Berichte, 1922, vol. 55, p. 1854
15
[ 79996-99-9 ]
[ 50672-84-9 ]
Yield
Reaction Conditions
Operation in experiment
80.4%
With 1,6-Hexanediamine; acetic acid In water at 100℃; for 3 h;
A 3 L three-necked flask was charged with 318 g of 4-bromo-1-bromomethylnaphthalene (II)371.5 g of hexamethylenediamine,795g glacial acetic acid,795g water,100 ° C reflux reaction 3h,Point plate, the reaction is completed,Rapid dropwise addition of 636 g concentrated hydrochloric acid,Drop back 0.5h.Cooling to room temperature,Add 4L of water,Stir for 3 h.filter,Filter cake and then 2L water beating 2h,Filter,Filter cake washed twice with water,Drained,40 ° C drying.Adding 318 g of ethanol to recrystallize,Dried to give 200.4 g of 4-bromo-1-naphthaldehyde (III)Yield 80.4percent.Wherein the molar ratio of 4-bromo-1-bromomethylnaphthalene (II) to hexamethylenetetramine is 1: 2.5,
Reference：
[1] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[2] Patent: CN106366018, 2017, A, . Location in patent: Paragraph 0040; 0041; 0042; 0043
[3] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[4] Chemische Berichte, 1922, vol. 55, p. 1854
[5] Organic Letters, 2008, vol. 10, # 14, p. 3105 - 3108
[6] Patent: WO2010/79077, 2010, A1, . Location in patent: Page/Page column 34
16
[ 79996-99-9 ]
[ 92616-49-4 ]
Yield
Reaction Conditions
Operation in experiment
78.87%
With ammonia; iodine In 1,4-dioxane at 30℃; for 3.5 h;
1-bromo-4- (bromomethyl) naphthalene was weighed(6.7 mmol, 1.0 eq) was added to 40 mL of dioxane and 4.5 g (130 mmol, 5 mL, 19.5 eq) of ammonia and 5.9 g (23.5 mmol, 3.5 eq) of iodine were added and the reaction was stirred at 30 ° C for 3.5 hours After the reaction was complete, the reaction was stopped, the reaction was quenched by adding 40 mL of purified water, extracted with ethyl acetate (3 x 30 mL), concentrated and recrystallized from ethyl acetate and petroleum ether 5: 1 to give 4-bromo-1- Cyanide 1.32 g, yield 78.87percent, purity 99.6percent.
Reference：
[1] Patent: CN105906530, 2016, A, . Location in patent: Paragraph 0113; 0114; 0115; 0116
[2] Patent: CN106366018, 2017, A,
With tetrabutylammomium bromide; In ethyl acetate; at 70℃; for 9h;
Weigh 4-Bromo-1-methylnaphthalene3.3 g (10.2 mmol, 1.5 eq) of tetrabutylammonium bromide was added to 30 mL of ethyl acetate and the mixture was refluxed at 70 C for 9 hours. After TLC showed that the starting material was completely reacted, The reaction was stopped. After filtering, the filter cake was stirred at room temperature for 2 hours with 30 mL of ethyl acetate and filtered to give 1.60 g of 1-bromo-4- (bromomethyl) naphthalene as a pale yellow solid in a yield of 77.43%.
73%
With N-Bromosuccinimide; dibenzoyl peroxide; In hexane; for 36h;Reflux; Inert atmosphere;
A suspension of 11 (35.37 g, 160 mmol), BPO (0.78 g, 3.2 mmol), and NBS (34.17 g, 192 mmol) in n-hexane (400 mL) was refluxed under N2 until the completion of reaction as indicated by TLC analysis (typically 36 h; once the reaction commenced, 0.78 g of BPO was added every 8 h until the reaction completed). The reaction mixture was cooled to room temperature while stirring, and the precipitates were collected via vacuum filtration. The precipitates were triturated successively with saturated aqueous NaHCO3 (500 mL x 2), water (800 mL x 2), and n-hexane (800 mL) to give rise to (4-bromonaphth-1-yl)methyl bromide 12. White solid; 35.04 g (73%); m.p. 104.5-106 C (literature value, 102-104 C [44]). 1H-NMR (DMSO-d6, 400 MHz) delta: 8.20-8.26 (m, 2H), 7.85 (d, J = 7.6 Hz, 1H), 7.71-7.77 (m, 2H), 7.62 (d, J = 7.6 Hz, 1H), 5.21 (s, 2H).
72%
With N-Bromosuccinimide; dibenzoyl peroxide; In hexane;Reflux;
To a dry 1 L round bottom flask was added n-hexane (400 mL) at room temperature, and B? (35.37 g, 160 mmol), benzoyl peroxide (BPO, 0.775 g, 3.2 mmol) and NBS (34.17 g, 192 mmol) were added with stirring. The resulting mixture was stirred and heated to reflux, until TLC indicated that the reaction was completed (0.775 g BPO was added once every 8 hours after the start of the reaction; the reaction was usually completed within 36 hours). (0087) After the reaction was completed, the system was cooled to room temperature, stirred for 2 hours, and then filtered by suction. The filter cake was added into 800 mL water, stirred at room temperature for 1 hour and filtered by suction, and the filtrate was discarded. The filter cake was added into 800 mL water again, stirred at room temperature for 1 hour and filtered by suction, and the filtrate was discarded. The resulting filter cake was pulped by stirring in 800 mL n-hexane for 2 hours and filtered by suction. The filter cake was dried to give a pure product of C? as a white solid, 34.56 g; yield: 72%; m.p.: 104.0-105.5 C. 1H NMR (DMSO-d6, 400 MHz), delta 8.20-8.26 (m, 2H), 7.86 (d, 1H, J=8.0 Hz), 7.72-7.78 (m, 2H), 7.62 (d, 1H, J=7.6 Hz), 5.21 (s, 2H).
500 g
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; at 70 - 78℃;
A 5 L four-necked flask was charged with 461.8 g of 4-bromo-1-methylnaphthalene (I)7.2kg of carbon tetrachloride,375.6 g of N-bromosuccinimide,20.5 g BP0,The temperature was raised to 70 to 78 C (preferably 77 C) and the reaction was refluxed overnight.Point plate,The reaction is complete.Cooled to room temperature,Filter,40 C spin dry solvent.Add 1200 g of ethanol,Heating up to 70 C Paul lh,Cooling to room temperature,Filter,Filter cake washed with ethanol,After draining,Dried at 35 C to give 500 g of 4-bromo-1-bromomethylnaphthalene (II)The two-step yield was 79% (based on 1-methylnaphthalene).
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 16h;Inert atmosphere;
Freshly crystalized BS (13.84 g, 77.80 mmol, 1.2 eq) was added to the solution of 1- bromo-4-methylnaphthalene (15.0 g, 67.84 mmol, 1.0 eq) and AIBN (1.11 g, 6.78 mmol, 0.1 eq) in carbon tetrachloride (150 mL) and the mixture was stirred at 80 C for 16 h under nitrogen atmosphere. After complete consumption of starting material, water was added to the reaction mixture and extracted with DCM. The organic layer was washed with water followed by brine, dried over anhydrous sodium sulfate, filtered, and the solvent evaporated from the filtrated under reduced pressure to obtain l-bromo-4-(bromomethyl)naphthalene. LCMS: Purity 96.83%
With N-Bromosuccinimide; dibenzoyl peroxide; In 2,3,4-trifluorotoluene; at 78℃; for 1.5h;Inert atmosphere;
Step A: A solution of benzoyl peroxide {87 mg) in trifiuorotoluene (40 mi) is refiuxed for 30 min under nitrogen. The reaction mixture is cooled to 78 0C and 1-bromo-4-methyl- naphthaiene (1.6 mi) an W-bromosuccinimide (2.0 g) are added. The reaction is stirred for 1.5 hours at 78 0C and filtered. The filtrate is concentrated in vacuo and the residue crystallized in heptane to yield 1~brom°-4-bromometnyi-naphfchaien8. The crude product is used in the next step without further purification.
With 1,6-Hexanediamine; acetic acid; In water; at 100℃; for 3h;
A 3 L three-necked flask was charged with 318 g of <strong>[79996-99-9]4-bromo-1-bromomethylnaphthalene</strong> (II)371.5 g of hexamethylenediamine,795g glacial acetic acid,795g water,100 C reflux reaction 3h,Point plate, the reaction is completed,Rapid dropwise addition of 636 g concentrated hydrochloric acid,Drop back 0.5h.Cooling to room temperature,Add 4L of water,Stir for 3 h.filter,Filter cake and then 2L water beating 2h,Filter,Filter cake washed twice with water,Drained,40 C drying.Adding 318 g of ethanol to recrystallize,Dried to give 200.4 g of 4-bromo-1-naphthaldehyde (III)Yield 80.4%.Wherein the molar ratio of <strong>[79996-99-9]4-bromo-1-bromomethylnaphthalene</strong> (II) to hexamethylenetetramine is 1: 2.5,
With sodium hydrogencarbonate; dimethyl sulfoxide; at 95℃; for 3h;
Step B: Sodium bicarbonate {1.4 g) is added to a solution of crude 1-bromo-4~bromomethyl~ naphthalene (2.5 g) in DMSO (25 rn.). The reaction is stirred for 3h at 95 "C and cooled down to room temperature. Water is added and the mixture is extracted with ethyi acetate. The organic phase is dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 4~bromo~naphtha.ene-1-carbafdehydtheta as colorless crystals.
A solution of 1-bromo-4-methylnaphthaleneacetate (14.98 g, 67.75 mmol), N-bromosuccinimide (12.1 g, 67.8 mmol) and 2,2'-azobis(isobutyronitrile) (50 mg) in carbon tetrachloride (50 ml) was heated under reflux for 0.5 hr. After cooling the reaction solution to room temperature, white precipitate was filtered off, and the precipitate was washed with diethyl ether. The solvent of the collected filtrate was evaporated under reduced pressure to give a crude product of <strong>[79996-99-9]1-bromo-4-(bromomethyl)naphthalene</strong> as a pale-yellow liquid. The obtained liquid was dissolved in N,N-dimethylformamide (30 ml), sodium acetate (11.1 g, 136 mmol) was added and the mixture was stirred at 60C for 6 hrs. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silic! a gel column chromatography (hexane/ethyl acetate=20/1-6/1) to give the objective substance. yellow liquid yield 14.97 g, 79%1H-NMR (CDCl3, 200MHz) delta 2.11 (3H, s), 5.53 (2H, s), 7.40 (1H, d, J = 7.8 Hz), 7.58-7.69 (2H, m), 7.77 (1H, d, J = 7.4 Hz), 7.97-8.05 (1H, m), 8.28-8.36 (1H, m); IR (neat) 1740, 1381, 1366, 1225, 1024, 824, 758 cm-1
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; for 0.5h;Heating / reflux;
A solution of 1-bromo-4-methylnaphthaleneacetate (14.98 g, 67.75 mmol), N-bromosuccinimide (12.1 g, 67.8 mmol) and 2,2'-azobis(isobutyronitrile) (50 mg) in carbon tetrachloride (50 ml) was heated under reflux for 0.5 hr. After cooling the reaction solution to room temperature, white precipitate was filtered off, and the precipitate was washed with diethyl ether. The solvent of the collected filtrate was evaporated under reduced pressure to give a crude product of 1-bromo-4-(bromomethyl)naphthalene as a pale-yellow liquid. The obtained liquid was dissolved in N,N-dimethylformamide (30 ml), sodium acetate (11.1 g, 136 mmol) was added and the mixture was stirred at 60C for 6 hrs. After cooling to room temperature, the reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silic! a gel column chromatography (hexane/ethyl acetate=20/1-6/1) to give the objective substance. yellow liquid yield 14.97 g, 79%1H-NMR (CDCl3, 200MHz) delta 2.11 (3H, s), 5.53 (2H, s), 7.40 (1H, d, J = 7.8 Hz), 7.58-7.69 (2H, m), 7.77 (1H, d, J = 7.4 Hz), 7.97-8.05 (1H, m), 8.28-8.36 (1H, m); IR (neat) 1740, 1381, 1366, 1225, 1024, 824, 758 cm-1
3-(4-bromo-naphthalen-1-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
Place diisopropylamine (1.24 ml, 8.88 mmol) in 15 ml of dry tetrahydrofurane. Chill to -780 C, add n-butillithium (3.55 ml, 8.88 mmol) dropwise, and stir for 15 minutes. Add 1-cyclohexyl-pyrrolidin-2-one (0.97 ml, 5.92 mmol) in 3 ml of tetrahydrofurane and stir for 30 minutes. Add <strong>[79996-99-9]1-bromo-4-bromomethyl-naphthalene</strong> (1.86 g, 6.21 mmol) and gradually warm the reaction mixture to room temperature. Quench with NH4Cl (saturated EPO <DP n="82"/>solution) and extract with ethyl acetate. Wash the extract with brine. Dry over magnesium sulfate, filter, and concentrate. Purify the residue by column chromatography to afford 1.86 g (81%) of the title compound: Mass spectrum (apci) m/z=287 (M+H).
With caesium carbonate; sodium iodide; In N,N-dimethyl-formamide; at 20℃; for 2.75h;
(S)-Methyl 5 -((6 -bromo-2 -methoxynaphthalen- 1 -yl)methyl)-3 -(tert-butoxycarbonyl amino)-4-oxo-2 ,3 ,4,5 -tetrahydrobenzo[b] [ 1 ,4]oxazepine-9-carboxylate Cs2C03 (1.02 g, 3.12 mmol, Eq: 1.05) and Nal (446 mg, 2.97 mmol, Eq: 1.0) were added to a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-4-oxo-2,3,4,5- tetrahydrobenzo[b][l ,4]oxazepine-9-carboxylate (1 g, 2.97 mmol, Eq: 1.00) and 6-bromo-l- (chloromethyl)-2-methoxynaphthalene (866 mg, 3.03 mmol, Eq: 1.02) in DMF (20 mL). The mixture was stirred at RT for 30 min. then heated to 50 C. After 75 min., the mixture was cooled to RT and diluted with 1/1 EtOAc/H20. The aqueous layer was extracted with EtOAc and the combined organic phases were washed with H20, brine, dried over Na2S04 and concentrated. The residue was purified by silica gel chromatography to afford (S)-methyl 5-((6-bromo-2- methoxynaphthalen-l-yl)methyl)-3-(tert-butoxycarbonylamino)-4-oxo-2,3,4,5-tetrahydro benzo[b][l,4]oxazepine-9-carboxylate (1.35 g, 75 %) as a white foam.
N-((4-bromonaphth-1-yl)methyl)phthalimide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
In N,N-dimethyl-formamide; at 100℃; for 12h;Inert atmosphere;
A mixture of 12 (33.00 g, 110 mmol) and potassium phthalimide (20.37 g, 110 mmol) in DMF (200 mL) was stirred at 100 C under N2 until the completion of reaction as indicated by TLC analysis (typically within 12 h). On cooling to room temperature, the reaction mixture was poured into ice-water (600 mL), and the aqueous mixture thus obtained was extracted with CH2Cl2 (150 mL x 3). The combined extracts were washed with 5% brine (100 mL x 5), dried over anhydrous Na2SO4, and evaporated on a rotary evaporator to afford a residue, which was recrystallized from ethanol to produce N-((4-bromonaphth-1-yl)methyl)phthalimide 13. White solid; 36.66 g (91%); m.p. 168.5-170 C. 1H-NMR (DMSO-d6, 400 MHz) delta: 8.30-8.33 (m, 1H), 8.17-8.21 (m, 1H), 7.83-7.92 (m, 4H), 7.80 (d, J = 8.0 Hz, 1H), 7.69-7.74 (m, 2H), 7.32 (d, J = 7.6 Hz, 1H), 5.23 (s, 2H).
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