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[ CAS No. 114772-40-6 ]

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Chemical Structure| 114772-40-6
Chemical Structure| 114772-40-6
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Product Details of [ 114772-40-6 ]

CAS No. :114772-40-6 MDL No. :MFCD06657561
Formula : C18H19BrO2 Boiling Point : 437°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :347.25 g/mol Pubchem ID :9906257
Synonyms :

Safety of [ 114772-40-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P271-P264-P280-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3261
Hazard Statements:H302+H312+H332-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 114772-40-6 ]

  • Upstream synthesis route of [ 114772-40-6 ]
  • Downstream synthetic route of [ 114772-40-6 ]

[ 114772-40-6 ] Synthesis Path-Upstream   1~20

  • 1
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  • [ 114772-40-6 ]
YieldReaction ConditionsOperation in experiment
85% With azobisisobutyronitrile; sodium acetate In acetic acid methyl ester; water; isopropyl alcohol; acetone EXAMPLE 4
268.0 kg of tert-butyl 4-methylbiphenyl-2'-carboxylate, 157.3 kg of DDH, 1.6 kg of AIBN, and 572 liters of methyl acetate are placed in a 1200-liter enamel stirring apparatus and the mixture is heated to 60° C. to 65° C.
As soon as the solution has become practically colorless, 458 liters of solvent are distilled off under normal pressure and then 530 liters of isopropanol, 148 liters of water, and 16.4 kg of sodium acetate (anhydrous) are added.
The resulting mixture is cooled to 15° C. to 25° C. and stirred for a further 1 hour.
The product precipitated is separated by centrifugation, washed with a mixture of 530 liters of acetone and 148 liters of water, and dried. Yield: 295 kg of tert-butyl 4-bromomethylbiphenyl-2'-carboxylate (85percent of theory).
80% With N-Bromosuccinimide; azobisisobutyronitrile; sodium acetate In acetic acid methyl ester; water; isopropyl alcohol EXAMPLE 1
241.2 kg of tert-butyl 4-methylbiphenyl-2'-carboxylate, 168.2 kg of NBS, 0.3 kg of AIBN, and 724 liters of methyl acetate are placed in a 1200-liter enamel stirring apparatus and the mixture is heated to 60° C. to 65° C.
The reaction mixture begins to boil and after about 80percent of the reaction time the NBS goes into solution.
As soon as the solution has become practically colorless, 603 liters of solvent are distilled off under normal pressure, and then 482 liters of isopropanol, 121 liters of water, and 14.8 kg of sodium acetate (anhydrous) are added.
The resulting mixture is cooled to 15° C. to 25° C. and stirred for a further 1 hour.
The product precipitated is separated by centrifugation, washed with a mixture of 482 liters of isopropanol and 121 liters of water, and dried. Yield: 250 kg of tert-butyl 4-bromomethylbiphenyl-2'-carboxylate (80percent of theory).
80% With N-Bromosuccinimide; azobisisobutyronitrile; sodium acetate In acetic acid methyl ester; water; acetone EXAMPLE 2
241.2 kg of tert-butyl 4-methylbiphenyl-2'-carboxylate, 168.2 kg of NBS, 0.3 kg of AIBN, and 724 liters of methyl acetate are placed in a 1200-liter enamel stirring apparatus and the mixture is heated to 60° C. to 65° C.
The reaction mixture begins to boil and after about 80percent of the reaction time the NBS goes into solution.
As soon as the solution has become practically colorless, 603 liters of solvent are distilled off under normal pressure and then 482 liters of acetone, 121 liters of water, and 14.8 kg of sodium acetate (anhydrous) are added.
The resulting mixture is cooled to 15° C. to 25° C. and stirred for a further 1 hour.
The product precipitated is separated by centrifugation, washed with a mixture of 482 liters of acetone and 121 liters of water, and dried. Yield: 250 kg of tert-butyl 4-bromomethylbiphenyl-2'-carboxylate (80percent of theory).
88% With sodium hydrogen sulfate; N-Bromosuccinimide; sodium hydrogencarbonate; sodium chloride; dibenzoyl peroxide In tetrachloromethane; hexane; water EXAMPLE 2
4-Bromomethyl-2'-t-butoxycarbonylbiphenyl
To a solution of 2-t-butoxycarbonyl-4'-methylbiphenyl (25.3 g, 95 mmol) in CCl4 (200 ml) were added freshly opened N-bromosuccinimide (17.6 g, 0.099 mole) and dibenzoyl peroxide (2.28 g, 0.0094 moles).
The mixture was refluxed for 4 hours, cooled to room temperature and filtered.
The filtrate was washed with sat. NaHSO3 (1*50 ml), sat. NaHCO3 (1*50 ml), water (1*50 ml), sat. NaCl (1*50 ml) and dried over MgSO4.
The solution was filtered, and concentrated in vacuo.
The residue was dissolved in 100 ml of hot hexane.
Crystallization gradually took place as the solution cooled.
The flask was finally cooled to -20° C. and the precipitate recovered by filtration.
The solid was washed with ice cold hexanes and dried in vacuo to give 27 g (88percent) of a white solid. 1 H-NMR (CDCl3): 1.23 (s, 9H), 4.53 (s, 2H), 7.2-7.5 (m, 7H), 7.68 (d, 1H).
88% With sodium hydrogen sulfate; N-Bromosuccinimide; sodium hydrogencarbonate; sodium chloride; dibenzoyl peroxide In tetrachloromethane; hexane; water 4-BROMOMETHYL-2'-t-BUTOXYCARBONYL-BIPHENYL
To a solution of 2-t-butoxycarbonyl-4'-methylbiphenyl (25.3 g, 95 mmol) in CCl4 (200 ml) were added freshly opened N-bromosuccinimide (17.6 g, 0.099 mole) and dibenzoyl peroxide (2.28 g, 0.0094 moles).
The mixture was refluxed for 4 hours, cooled to room temperature and filtered.
The filtrate was washed with sat. NaHSO3 (1*50 ml), sat. NaHCO3 (1*50 ml), water (1*50 ml), sat. NaCl (1*50 ml) and dried over MgSO4.
The solution was filtered and concentrated in vacuo.
The residue was dissolved in 100 ml of hot hexane.
Crystallization gradually took place as the solution cooled.
The flask was finally cooled to -20° C. and the precipitate recovered by filtration.
The solid was washed with ice cold hexanes and dried in vacuo to give 27 g (88percent) of a white solid. 1 H-NMR (CDCl3): 1.23 (s, 9H), 4.53 (s, 2H), 7.2-7.5 (m, 7H), 7.68 (d, 1H).
88% With sodium hydrogen sulfate; N-Bromosuccinimide; sodium hydrogencarbonate; sodium chloride; dibenzoyl peroxide In tetrachloromethane; hexane; water 4-Bromomethyl-2'-t-butoxycarbonylbiphenyl
To a solution of 2-t-butoxycarbonyl-4'-methylbiphenyl (25.3 g, 95 mmol) in CCl4 (200 ml) were added freshly opened N-bromosuccinimide (17.6 g, 0.099 mole) and dibenzoyl peroxide (2.28 g, 0.0094 moles).
the mixture was refluxed for 4 hours, cooled to room temperature and filtered.
The filtrate was washed with sat. NaHSO3 (1*50 ml), sat. NaHCO3 (1*50 ml), water (1*50 ml), sat. NaCl (1*50 ml) and dried over MgSO4.
The solution was filtered, and concentrated in vacuo.
The residue was dissolved in 100 ml of hot hexane.
Crystallization gradually took place as the solution cooled.
The flask was finally cooled to -20° C. and the precipitate recovered by filtration.
The solid was washed with ice cold hexanes and dried in vacuo to give 27 g (88percent) of a white solid. 1 H-NMR (CDCl3): 1.23 (s, 9H), 4.53 (s, 2H),
7.2-7.5 (m, 7H), 7.68 (d, 1H).

Reference: [1] Patent: US2002/95042, 2002, A1,
[2] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 897 - 906
[3] Patent: US2002/95042, 2002, A1,
[4] Patent: US2002/95042, 2002, A1,
[5] Patent: WO2013/78237, 2013, A1, . Location in patent: Page/Page column 78
[6] ACS Medicinal Chemistry Letters, 2019, vol. 10, # 1, p. 86 - 91
[7] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
[8] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2172 - 2181
[9] Patent: US2001/20100, 2001, A1,
[10] Patent: US5236928, 1993, A,
[11] Patent: US5238942, 1993, A,
[12] Patent: US5250521, 1993, A,
[13] Patent: US5102880, 1992, A,
[14] Patent: US2008/269305, 2008, A1, . Location in patent: Page/Page column 42
[15] Patent: US2008/188533, 2008, A1, . Location in patent: Page/Page column 39
[16] Patent: US2008/318951, 2008, A1, . Location in patent: Page/Page column 44
[17] Patent: WO2009/35543, 2009, A1, . Location in patent: Page/Page column 88-89
[18] Patent: US2010/22599, 2010, A1, . Location in patent: Page/Page column 49-50
[19] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[20] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
[21] Patent: US2012/309757, 2012, A1, . Location in patent: Page/Page column 90
[22] Patent: WO2015/161108, 2015, A1, . Location in patent: Page/Page column 241
[23] Patent: US5240928, 1993, A,
[24] Patent: US5332744, 1994, A,
  • 2
  • [ 50-00-0 ]
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YieldReaction ConditionsOperation in experiment
81.9%
Stage #1: With zinc dibromide In dichloromethane at 30 - 35℃; for 0.333333 h;
Stage #2: With phosphorus pentabromide In tetrachloromethane; dichloromethane
In the four reaction flask was added biphenyl-2-carboxylic acid isopropyl ester feedstock 17g (70.7mmol), paraformaldehyde 2.75g (91.7mmol) and methylene chloride 120g, controlling the temperature 30 ~ 35 (53.3 mmol) of zinc bromide was added under stirring, and the reaction was stirred for 20 min. Slowly dropped PBr515.5g (36mmol) and carbon tetrachloride 15g mixed solution, the dropping time of about 1h, the addition was complete, HPLC analysis of raw material sampling the reaction was complete, about 3 ~ 4h. After cooling to 10 ° C, the oil layer was washed three times with ice water, and dried to recover methylene chloride. The crude product was recrystallized to give 19.3 g of pure product of 4'-bromomethylbiphenyl-2-carboxylic acid isopropyl ester in a yield of 81.9percent.
Reference: [1] Patent: CN105330541, 2016, A, . Location in patent: Paragraph 0056; 0058
  • 3
  • [ 7148-03-0 ]
  • [ 114772-40-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2172 - 2181
[2] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
[3] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[4] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
[5] ACS Medicinal Chemistry Letters, 2019, vol. 10, # 1, p. 86 - 91
  • 4
  • [ 55666-42-7 ]
  • [ 114772-40-6 ]
Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 897 - 906
[2] Patent: US2012/309757, 2012, A1,
[3] Patent: WO2013/78237, 2013, A1,
[4] Patent: WO2015/161108, 2015, A1,
  • 5
  • [ 88-65-3 ]
  • [ 114772-40-6 ]
Reference: [1] Patent: US2012/309757, 2012, A1,
[2] Patent: WO2013/78237, 2013, A1,
[3] Patent: WO2015/161108, 2015, A1,
  • 6
  • [ 145319-09-1 ]
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 6, p. 1913 - 1917
  • 7
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Reference: [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 7, p. 897 - 906
  • 8
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Reference: [1] Journal of Medicinal Chemistry, 1993, vol. 36, # 15, p. 2172 - 2181
  • 9
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 10
  • [ 114772-35-9 ]
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 11
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 12
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 13
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 14
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Reference: [1] Journal of Medicinal Chemistry, 1991, vol. 34, # 8, p. 2525 - 2547
  • 15
  • [ 100-47-0 ]
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Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[2] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
  • 16
  • [ 214360-47-1 ]
  • [ 114772-40-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[2] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
  • 17
  • [ 114772-53-1 ]
  • [ 114772-40-6 ]
Reference: [1] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374,17
[2] European Journal of Medicinal Chemistry, 2012, vol. 55, p. 358 - 374
  • 18
  • [ 106-38-7 ]
  • [ 110349-26-3 ]
  • [ 114772-40-6 ]
Reference: [1] Patent: US5332744, 1994, A,
  • 19
  • [ 947-84-2 ]
  • [ 114772-40-6 ]
Reference: [1] Patent: CN105330541, 2016, A,
  • 20
  • [ 114772-36-0 ]
  • [ 901768-33-0 ]
  • [ 114772-40-6 ]
Reference: [1] Journal of Chemical Research, 2010, # 2, p. 95 - 97
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