[ CAS No. 7398-42-7 ]

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2D
Chemical Structure| 7398-42-7
Chemical Structure| 7398-42-7
Structure of 7398-42-7

Quality Control of [ 7398-42-7 ]

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SDS

Product Details of [ 7398-42-7 ]

CAS No. :7398-42-7MDL No. :MFCD07783030
Formula :C10H11BrO2Boiling Point :-
Linear Structure Formula :C10H11O2BrInChI Key :-
M.W :243.10Pubchem ID :11770640
Synonyms :

Computed Properties of [ 7398-42-7 ]

TPSA : 26.3 H-Bond Acceptor Count : 2
XLogP3 : - H-Bond Donor Count : 0
SP3 : 0.30 Rotatable Bond Count : 4

Safety of [ 7398-42-7 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 7398-42-7 ]

  • Upstream synthesis route of [ 7398-42-7 ]
  • Downstream synthetic route of [ 7398-42-7 ]

[ 7398-42-7 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
100% at 20℃; for 2.00 h; To a stirred suspension of 2-(4-(bromomethyl)phenyl)acetic acid (5.00 g, 21.8 mmol, 1.0 eq.) in methanol (75 mL) was added chlorotrimethylsilane (0.64 mL, 5.02 mmol, 0.23 eq.) at room temperature. The resulting mixture was stirred at room temperature for 2 hr, at which time the reaction was a clear colorless solution. The volatile material was removed under reduced pressure, the residue dissolved in methanol (25 mL), and the volatile material was removed under reduced pressure. This process was repeated two additional times to afford methyl 2-(4-(bromomethyl)phenyl)acetate as an orange solid (5.30 g, quantitative yield). ]H NMR (CDC13, 500 MHz) δ 7.37-7.33 (m, 2H), 7.26-7.24 (m, 2H), 4.48 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H). [Lit. /. Med. Chem. 2009, 52, 1180-9.]
99% at 20℃; for 8.00 h; Step (ii); 4-Bromomethylphenylacetic acid methyl ester; [Show Image] To 4-bromomethylphenylacetic acid 25g (109mmol) in methanol (120ml) was added thionyl chloride 120μl (1.64mmol) and the mixture was stirred at room temperature for 8 hours. After removal of the solvent in vacuo, the residue was neutralized with aqueous saturated sodium bicarbonate, and the mixture was extracted with ethyl acetate (300ml). The organic layer was washed aqueous saturated sodium bicarbonate, (50ml) and saturated brine (20ml), successively and dried over magnesium sulfate. The solvent was removed in vacuo to give the subtitled compound 25g as colorless crystals. Yield 99percent 1H NMR (CDCl3) δ 7.36 (2H, t, J= 8.1 Hz), 7.26 (2H, d, J= 8.1 Hz), 4.48 (2H, s), 3.69 (3H, s), 3.62 (2H, s).
98.6% at 0℃; for 1.00 h; [7101 Step 1: Synthesis of methyl 2-(4-(bromomethyl)phenyl)acetate[7111 2-(4-(bromomethyl)phenyl)acetic acid (3.000 g, 13.096 mmol) was dissolved in methanol (30 mL), and SOC12(1.900 mL, 26.193 mmol) was added thereto at 0 °C, followed by stirring at the same temperature for 1 hour. Then, the reaction mixture was concentrated under reduced pressure to remove the solvent. A saturated aqueous solution of sodium hydrogen carbonate was added to the concentrate, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to yield the desired compound (3.140 g, 98.6 percent) as a colorless oil.
96% at 20℃; for 16.00 h; a) Methyl 2- r4-(bromomethyl)phenyll acetate (1-72) Thionyl chloride (48 μ; 0.65 mmol; 0.017 eq) was added to a solution of 2-[4- (bromomethyl)phenyl] acetic acid (10 g; 43.07 mmol; 1 eq) in methanol (48 mL). The reaction mixture was stirred at room temperature for 16 hours, then, concentrated to dryness. The residue was taken up in saturated sodium hydro genocarbonate (150 mL) and the resulting aqueous layer was extracted with ethyl acetate (3 x 100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound, methyl 2-[4- (bromomethyl)phenyl] acetate was obtained in 96percent yield (10.2 g) as a white solid. 1H NMR (CDC13): δ (ppm) 3.68 (s, 2H), 3.75 (s, 3H), 4.54 (s, 2H), 7.37 (m, 4H).
79% at 60℃; for 3.00 h; A mixture of 2- [4-(bromomethyl)phenyl] acetic acid (3 g, 13.10 mmol), methanol (100 mL), thionyl chloride (2.3 g, 19.33 mmol) was stirred for 3 h at 60°C. The resulting mixture was concentrated under vacuum. This resulted in the title compound (2.5 g, 79percent) as colorless oil.
58% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0 - 20℃; To a stirring solution of 14 in tetrahydrofuran (0.6 M) at 0 C. under nitrogen was added dimethylaminopyridine (0.2 eq), methanol (2.2 eq) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (2.2 eq). The reaction was stirred at room temperature overnight. The tetrahydrofuran was removed under reduced pressure. The resulting oil was partitioned between ethyl acetate and saturated sodium bicarbonate. The phases were separated and the organic phase was washed with saturated sodium bicarbonate (1?), 1N hydrochloric acid (1?), brine (1?), dried over sodium sulfate, filtered and concentrated in vacuo to afford the product. (58percent) 1H NMR (400 MHz, DMSO-d6) ? 7.38 (d, 2H), 7.27 (d, 2H), 4.75 (s, 2H), 3.69 (s, 2H), 3.61 (s, 3H).

Reference: [1] Patent: WO2014/66659, 2014, A1. Location in patent: Paragraph 0616
[2] Patent: EP1939199, 2008, A1. Location in patent: Page/Page column 96-97
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 4, p. 1180 - 1189
[4] Patent: WO2015/137750, 2015, A1. Location in patent: Paragraph 710; 711
[5] Patent: WO2013/171281, 2013, A1. Location in patent: Page/Page column 169
[6] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1768 - 1792
[7] Patent: WO2018/96159, 2018, A1. Location in patent: Paragraph 0307-0310
[8] Heterocyclic Communications, 2008, vol. 14, # 3, p. 129 - 136
[9] Synthesis, 2006, # 3, p. 405 - 410
[10] Journal of Medicinal Chemistry, 2017, vol. 60, # 18, p. 7703 - 7724
[11] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 10, p. 2647 - 2652
[12] Patent: US2004/254156, 2004, A1. Location in patent: Page 21
[13] Patent: WO2007/12479, 2007, A2. Location in patent: Page/Page column 36
[14] Patent: EP2251380, 2010, A2. Location in patent: Page/Page column 19-20
[15] Patent: WO2012/80730, 2012, A1. Location in patent: Page/Page column 36
[16] Patent: WO2014/178001, 2014, A1. Location in patent: Page/Page column 59
[17] Patent: US2014/275070, 2014, A1. Location in patent: Paragraph 0175; 0176
[18] Organic and Biomolecular Chemistry, 2016, vol. 14, # 38, p. 9055 - 9062
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YieldReaction ConditionsOperation in experiment
94.3% at 20℃; for 1.00 h; Inert atmosphere In a 100 mL round bottom flask, a solution of 2-(4-(bromomethyl)phenyl)acetic acid (2.5 g, 10.91 mmol) in MeOH (50 mL) was treated with TMSC1 (0.2 mL) under nitrogen atmosphere. The reaction mixture was stirred for 1 h at RT. Upon completion of reaction (TLC), the solvent was removed under reduced pressure. The residue obtained was dissolved in methanol and concentrated under reduced pressure to give the title compound. Yield: 2.5 g (94.3percent). (0727) 1H NMR (300 MHz, CDC : δ 7.36 (d, J = 8.1 Hz, 2H), 7.26 (d, J = 8.4 Hz, 2H), 4.48 (s, 2H), 3.69 (s, 3H), 3.62 (s, 2H)
Reference: [1] Patent: WO2016/57660, 2016, A1. Location in patent: Page/Page column 77; 78
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Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 3758 - 3764
[2] Patent: US5374641, 1994, A
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Reference: [1] Patent: EP1273571, 2003, A1
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Reference: [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 48, p. 12000 - 12004[2] Angew. Chem., 2012, vol. 124, # 48, p. 12166 - 12170,4
[3] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 18, p. 2149 - 2152
[4] Journal of Medicinal Chemistry, 2001, vol. 44, # 5, p. 703 - 714
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Reference: [1] Patent: EP1389460, 2004, A1. Location in patent: Page/Page column 28
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Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 3758 - 3764
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