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[ CAS No. 1242822-57-6 ] {[proInfo.proName]}

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Chemical Structure| 1242822-57-6
Chemical Structure| 1242822-57-6
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CAS No. :1242822-57-6 MDL No. :MFCD18390310
Formula : C7H6BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 221.48 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 1242822-57-6 ]

* 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.

  • Downstream synthetic route of [ 1242822-57-6 ]

[ 1242822-57-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 64622-16-8 ]
  • [ 1242822-57-6 ]
YieldReaction ConditionsOperation in experiment
59.6% With potassium borohydride; In ethanol; at 0℃; for 2h; To a solution of <strong>[64622-16-8]2-bromo-6-chlorobenzaldehyde</strong> (i-8a) (1.5 g, 6.8 mmol) in EtOH (20 mL) was added KBH4 (1.49 g, 3.4 mmol) in portions at 0 C. The mixture was stirred at 0 C for 2 h. The solvent was removed in vacuo, and the residue was partitioned between water (10 mL) and DCM (5 mL). The aqueous layer was extracted with DCM (5 mL x 3). The combined organic layers were dried over anhydrous Na2S04 and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (PE / EtOAc = 3 / 1) to afford the title compound (0.9 g, yield: 59.6%) as colorless oil. LCMS (ESI) calc'd for CyHgBrClO [M+H]+: 221, found: 221.
59.6% With potassium borohydride; In ethanol; at 0℃; for 2h; i). Preparation of (2-bromo-6-chlorophenyl)methanol (i-8b) To a solution of <strong>[64622-16-8]2-bromo-6-chlorobenzaldehyde</strong> (i-8a) (1.5 g, 6.8 mmol) in EtOH (20 mL) was added KBH4 (1.49 g, 3.4 mmol) in portions at 0 C. The mixture was stirred at 0 C. for 2 h. The solvent was removed in vacuo, and the residue was partitioned between water (10 mL) and DCM (5 mL). The aqueous layer was extracted with DCM (5 mL*3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (PE/EtOAc=3/1) to afford the title compound (0.9 g, yield: 59.6%) as colorless oil. LCMS (ESI) calc'd for C7H6BrClO [M+H]+: 221. found: 221.
  • 2
  • [ 93224-85-2 ]
  • [ 1242822-57-6 ]
YieldReaction ConditionsOperation in experiment
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 80℃; for 17h; Step 1. Preparation of (2-bromo-6-chlorophenyl)methanol (i-6a) [00149] To a solution of <strong>[93224-85-2]2-bromo-6-chlorobenzoic acid</strong> (20 g, 85 mmol) in THF (200 mL) was added BH3 DMS (42.5 mL, 425 mmol) slowly at 0 C. The resulting solution was heated at 80 C for 17 h. The reaction was cooled and quenched with MeOH (100 mL) and NaCIO (aq., 100 mL) carefully, then most of THF and MeOH were removed under reduced pressure and the remaining aqueous phase was filtered. The filtrate was extracted with EtOAc (4x30 mL). The combined organic layers were washed with brine (50 mL), dried over Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether: EtOAc = 50: 1 - 20: 1) to give the title compound. XH NMR (400 MHz, CDC13) delta 7.52 (d, J = 8.0 Hz, 1H), 7.38 (d, J= 8.0 Hz, 1H), 7.12 (t, J= 8.0 Hz, 1H), 4.99 (d, J = 3.5 Hz, 2H), 2.08-2.29 (m, 1H).
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 80℃; for 17h; To a solution of <strong>[93224-85-2]2-bromo-6-chlorobenzoic acid</strong> (20 g, 85 mmol) in THF (200 mL) was added BH3.DMS (42.5 mL, 425 mmol) slowly at 0 C. The resulting solution was heated at 80 C. for 17 h. The reaction was cooled and quenched with MeOH (100 mL) and NaClO (aq., 100 mL) carefully, then most of THF and MeOH were removed under reduced pressure and the remaining aqueous phase was filtered. The filtrate was extracted with EtOAc (4*30 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether:EtOAc=50:1-20:1) to give the title compound. 1H NMR (400 MHz, CDCl3) delta 7.52 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 4.99 (d, J=3.5 Hz, 2H), 2.08-2.29 (m, 1H).
With dimethylsulfide borane complex; In tetrahydrofuran; at 0 - 80℃; for 17h; To a solution of <strong>[93224-85-2]2-bromo-6-chlorobenzoic acid</strong> (20 g, 85 mmol) in THF (200 mL) was added BH3.DMS (42.5 mL, 425 mmol) slowly at 0 C. The resulting solution was heated at 80 C. for 17 h. The reaction was cooled and quenched with MeOH (100 mL) and NaClO (aq., 100 mL) carefully, then most of THF and MeOH were removed under reduced pressure and the remaining aqueous phase was filtered. The filtrate was extracted with EtOAc (4*30 mL). The combined organic layers were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (petroleum ether:EtOAc=50:1-20:1) to give the title compound. 1H NMR (400 MHz, CDCl3) delta 7.52 (d, J=8.0 Hz, 1H), 7.38 (d, J=8.0 Hz, 1H), 7.12 (t, J=8.0 Hz, 1H), 4.99 (d, J=3.5 Hz, 2H), 2.08-2.29 (m, 1H).
With dimethylsulfide borane complex; In tetrahydrofuran; at 80℃; for 17h; BH 3 .DMS (42.5 mL, 425 mmol) at 0 C. was slowly added to a solution of <strong>[93224-85-2]2-bromo-6-chlorobenzoic acid</strong> (20 g, 85 mmol) in THF (200 mL).The resulting solution was heated at 80 C. for 17 h. The reaction was cooled and carefully quenched with MeOH (100 mL) and NaClO (aq, 100 mL), then THF and MeOHThe residue was removed under reduced pressure and the remaining aqueous phase was filtered. The filtrate was extracted with EtOAc (4 × 30 mL). The combined organic layers were washed with brine (50 mL), dried over Na 2 SO 4, filtered and dried in vacuoAnd concentrated. The residue was purified by silica gel column chromatography (petroleum ether: EtOAc = 50: 1 to 20: 1) to give the title compound.

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