Home Cart 0 Sign in  

[ CAS No. 812667-44-0 ]

{[proInfo.proName]} ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
2D
Chemical Structure| 812667-44-0
Chemical Structure| 812667-44-0
Structure of 812667-44-0 *Storage: {[proInfo.prStorage]}

Quality Control of [ 812667-44-0 ]

Related Doc. of [ 812667-44-0 ]

SDS
Alternatived Products of [ 812667-44-0 ]
Alternatived Products of [ 812667-44-0 ]

Product Details of [ 812667-44-0 ]

CAS No. :812667-44-0MDL No. :MFCD12913570
Formula : C8H8BrNO2 Boiling Point : 305.9°C at 760 mmHg
Linear Structure Formula :-InChI Key :N/A
M.W :230.06Pubchem ID :-
Synonyms :

Computed Properties of [ 812667-44-0 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 812667-44-0 ]

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

Application In Synthesis of [ 812667-44-0 ]

  • Upstream synthesis route of [ 812667-44-0 ]
  • Downstream synthetic route of [ 812667-44-0 ]

[ 812667-44-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 812667-44-0 ]
  • [ 330793-38-9 ]
YieldReaction ConditionsOperation in experiment
92% With trifluorormethanesulfonic acid; triethylamine In dichloromethane at 0 - 20℃; for 1.5 h; To a solution of 9.22g (40.1mmol) of the compound obtained in the Manufacturing Example 1 in 200mL of anhydrous dichloromethane were added 11.17mL (80.2mmol) of triethyamine and 8.09mL of anhydrous trifluoromethanesulfonic acid at 0°C, and the mixture was stirred for 30 minutes at the same temperature and for 1 hour at room temperature. Then, water was added to the reaction mixture and the mixture was extracted with dichloromethane. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent: chloroform) to give 7.84g (92percent) of the title compound.
53%
Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25 h;
Stage #2: With O-phenyl phosphorodichloridate In dichloromethane at 0 - 20℃; for 1.2 h;
[00198] Step 2: A solution of 4-bromo-2-methoxybenzamide (508 mg, 2.21 mmol) in anhydrous DCM (10 mL) was cooled to 0 0C and then treated with 1,8- diazabicyclo(5.4.0)undec-7-ene (0.991 mL, 6.62 mmol). The mixture was stirred at 0 0C for 15 min, and then treated with phenyl dichlorophosphate (0.660 mL, 4.42 mmol) over 2 min. The reaction was stirred at 0 0C for 10 min, and then warmed to RT where it stirred for 1 h. After this time, the mixture was partitioned betweenDCM (10 mL) and saturated NH4Cl (20 mL). The aqueous phase was extracted with DCM. The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by flash chromatography (12 g SiO2 column; 0- 30percent EtO Ac/Hex gradient) to give 4-bromo-2-methoxybenzonitrile (250 mg, 1.18 mmol, 53 percent yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 7.40 (1 H, s), 7.16 (1 H, s), 7.12 (1 H, s), 3.91 (3 H, s).
53%
Stage #1: With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 0℃; for 0.25 h;
Stage #2: With O-phenyl phosphorodichloridate In dichloromethane at 0 - 20℃; for 1.2 h;
[00198] Step 2: A solution of 4-bromo-2-methoxybenzamide (508 mg, 2.21 mmol) in anhydrous DCM (10 mL) was cooled to 0 0C and then treated with 1,8- diazabicyclo(5.4.0)undec-7-ene (0.991 mL, 6.62 mmol). The mixture was stirred at 0 0C for 15 min, and then treated with phenyl dichlorophosphate (0.660 mL, 4.42 mmol) over 2 min. The reaction was stirred at 0 0C for 10 min, and then warmed to RT where it stirred for 1 h. After this time, the mixture was partitioned betweenDCM (10 mL) and saturated NH4Cl (20 mL). The aqueous phase was extracted with DCM. The combined extracts were dried (MgSO4) and concentrated to give the crude product, which was purified by flash chromatography (12 g SiO2 column; 0- 30percent EtO Ac/Hex gradient) to give 4-bromo-2-methoxybenzonitrile (250 mg, 1.18 mmol, 53 percent yield) as a white solid. 1H-NMR (400 MHz, CDCl3) δ ppm 7.40 (1 H, s), 7.16 (1 H, s), 7.12 (1 H, s), 3.91 (3 H, s).
Reference: [1] Patent: WO2004/111053, 2004, A1, . Location in patent: Page/Page column 20-21
[2] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 100
[3] Patent: WO2008/42925, 2008, A1, . Location in patent: Page/Page column 100
Historical Records