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Product Details of [ 124276-67-1 ]

CAS No. :124276-67-1 MDL No. :MFCD01314308
Formula : C10H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :BWPZBXQENXGRQV-UHFFFAOYSA-N
M.W : 222.08 Pubchem ID :2795273
Synonyms :

Safety of [ 124276-67-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P261-P270-P271-P264-P280-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 124276-67-1 ]

* 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.

  • Upstream synthesis route of [ 124276-67-1 ]
  • Downstream synthetic route of [ 124276-67-1 ]

[ 124276-67-1 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 124276-67-1 ]
  • [ 847361-67-5 ]
Reference: [1] Journal of the American Chemical Society, 2011, vol. 133, # 32, p. 12386 - 12389
[2] Patent: WO2006/133559, 2006, A1,
  • 2
  • [ 124276-67-1 ]
  • [ 345965-52-8 ]
YieldReaction ConditionsOperation in experiment
69%
Stage #1: With potassium hydroxide In ethylene glycol at 160℃; for 6 h;
Stage #2: With hydrogenchloride In water; ethylene glycol
A mixture of compound XV-2 (7.5 g, 33.78 mmol), KOH (7.6 g, 135 mmol) and ethylene glycol (50 mL) were heated to 160°C for 6 hrs. The mixture was cooled to room temperature, water (200 mL) was added and the mixture was acidified to pH=3~4 with aq. HCl (2 N) to precipitate the product. The product was collected by filtration to yield compound XV- 3 (5.6 g, yield 69percent). MS (ESI) m/z (M+H)+ 240.
330 mg With sodium hydroxide In ethanol; water at 100℃; Step 2:
Preparation of 1-(4-bromophenyl)cyclopropancarboxylic acid
1-(4-bromophenyl)cyclopropancarbonitrile (256 mg) prepared in Step 1 was dissolved in a mixed solution of ethanol (2.5 mL) and an aqueous solution of sodium hydroxide (1.2 mL, 25percent w/w).
The mixture was heated to 100°C, and stirred overnight.
Upon completion of the reaction, ice was added to the reaction mixture, followed by addition of dichloromethane and 1N aqueous solution of hydrochloric acid.
The organic layer thus formed was separated, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure to obtain the target compound as oil (330 mg).
1H NMR (300 MHz, DMSO-d6): δ 12.38 (s, 1H), 7.46(d, 2H), 7.26(d, 2H), 1.42(q, 2H), 1.11 (q, 2H)
330 mg With sodium hydroxide In ethanol; water at 100℃; Step 2:
Preparation of 1-(4-bromophenyl)cyclopropancarboxylic acid
1-(4-bromophenyl)cyclopropancarbonitrile (256 mg) prepared in Step 1 was dissolved in a mixed solution of ethanol (2.5 mL) and an aqueous solution of sodium hydroxide (1.2 mL, 25percent w/w).
The mixture was heated to 100° C., and stirred overnight.
Upon completion of the reaction, ice was added to the reaction mixture, followed by addition of dichloromethane and 1N aqueous solution of hydrochloric acid.
The organic layer thus formed was separated, dried over anhydrous sodium sulfate, filtered and distilled under a reduced pressure to obtain the target compound as oil (330 mg).
1H NMR (300 MHz, DMSO-d6): δ 12.38 (s, 1H), 7.46 (d, 2H), 7.26 (d, 2H), 1.42 (q, 2H), 1.11 (q, 2H)
Reference: [1] Patent: US6359135, 2002, B1, . Location in patent: Page column 113
[2] Patent: US6369225, 2002, B1, . Location in patent: Page column 42, 112
[3] Journal of Medicinal Chemistry, 2010, vol. 53, # 16, p. 6003 - 6017
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 887 - 892
[5] Patent: WO2013/25733, 2013, A1, . Location in patent: Paragraph 0490
[6] Patent: WO2004/814, 2003, A1, . Location in patent: Page 88
[7] Patent: WO2004/48374, 2004, A1, . Location in patent: Page 51
[8] Patent: WO2005/19161, 2005, A1, . Location in patent: Page/Page column 51
[9] Patent: WO2005/21487, 2005, A1, . Location in patent: Page/Page column 57
[10] Patent: WO2005/56529, 2005, A1, . Location in patent: Page/Page column 46
[11] Patent: WO2010/141761, 2010, A2, . Location in patent: Page/Page column 47
[12] Patent: US2011/82164, 2011, A1, . Location in patent: Page/Page column 24
[13] Patent: US2011/82181, 2011, A1, . Location in patent: Page/Page column 16
[14] Patent: WO2012/78593, 2012, A2, . Location in patent: Page/Page column 123-124
[15] Patent: WO2012/78805, 2012, A1, . Location in patent: Page/Page column 91-92
[16] Patent: US2012/258987, 2012, A1, . Location in patent: Page/Page column 41
[17] Patent: WO2013/189865, 2013, A1, . Location in patent: Page/Page column 27-28
[18] Patent: EP2738174, 2014, A2, . Location in patent: Paragraph 0182; 0183
[19] Patent: US2014/163226, 2014, A1, . Location in patent: Paragraph 0330-0332
[20] Patent: WO2006/133559, 2006, A1, . Location in patent: Page/Page column 33-34
[21] Advanced Synthesis and Catalysis, 2018, vol. 360, # 22, p. 4306 - 4311
  • 3
  • [ 107-21-1 ]
  • [ 124276-67-1 ]
  • [ 345965-52-8 ]
Reference: [1] Patent: US6369261, 2002, B1, . Location in patent: Page column 111
  • 4
  • [ 124276-67-1 ]
  • [ 1215205-50-7 ]
Reference: [1] Patent: US2011/82164, 2011, A1,
[2] Patent: WO2012/78593, 2012, A2,
[3] Patent: US2011/82181, 2011, A1,
[4] Patent: WO2012/78805, 2012, A1,
[5] Patent: US2012/258987, 2012, A1,
  • 5
  • [ 124276-67-1 ]
  • [ 1257213-52-7 ]
Reference: [1] Patent: US2011/82164, 2011, A1,
[2] Patent: WO2012/78593, 2012, A2,
[3] Patent: US2011/82181, 2011, A1,
[4] Patent: WO2012/78805, 2012, A1,
[5] Patent: US2012/258987, 2012, A1,
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