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CAS No. : | 321848-65-1 | MDL No. : | MFCD08234770 |
Formula : | C12H14BrNO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | HVCLJUVMOVVZBS-NSHDSACASA-N |
M.W : | 268.15 | Pubchem ID : | 57377187 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 | UN#: | N/A |
Hazard Statements: | H315-H319 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | Stage #1: (4R)-2-(2-bromophenyl)-4-isopropyl-4,5-dihydro-1,3-oxazole With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: With selenium In tetrahydrofuran; pentane at -78 - 0℃; for 1h; Stage #3: Cinnamyl bromide In tetrahydrofuran; pentane at 0℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 2-bromo-<i>N</i>-(1-hydroxymethyl-2-methyl-propyl)-benzamide With Vilsmeier reagent In pyridine at 20℃; for 2h; Stage #2: With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 3h; Stage #3: With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran Heating; Further stages.; | |
With thionyl chloride In dichloromethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: SOCl2 / CH2Cl2 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 2: SOCl2 / CH2Cl2 | ||
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 12 h / 0 - 20 °C 2: thionyl chloride / dichloromethane / 4 h / 0 - 64 °C 3: water; sodium hydroxide / methanol / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C 1.2: Se / tetrahydrofuran; pentane / 1 h / -78 - 0 °C 1.3: 73 percent / tetrahydrofuran; pentane / 1 h / 0 °C 2.1: 4 Angstroem molecular sieves; TBHP / vanadyl acetylacetonate / CH2Cl2; decane / -50 °C 2.2: Bu3P / CH2Cl2; decane / 0.17 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C 1.2: Se / tetrahydrofuran; pentane / 1 h / -78 - 0 °C 1.3: 73 percent / tetrahydrofuran; pentane / 1 h / 0 °C 2.1: 4 Angstroem molecular sieves; TBHP / vanadyl acetylacetonate / CH2Cl2; decane / -50 °C 2.2: Bu3P / CH2Cl2; decane / 0.17 h / -10 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: (R)-2-amino-3-methylbutanol; 2-bromobenzoic acid chloride With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; Stage #2: With methanesulfonyl chloride In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
8% | With bis-triphenylphosphine-palladium(II) chloride; triethylamine In tetrahydrofuran at 50℃; for 24h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56.2% | Stage #1: (4R)-2-(2-bromophenyl)-4-isopropyl-4,5-dihydro-1,3-oxazole With bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran for 0.0833333h; Inert atmosphere; Schlenk technique; Stage #2: ferrocenylethynylcopper In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: (4R)-2-(2-bromophenyl)-4-isopropyl-4,5-dihydro-1,3-oxazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: mercury dichloride at -78 - 20℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate In toluene for 48h; Inert atmosphere; Reflux; | 1.2 (2) Preparation of chiral bidentate ligand The chiral o-bromobenzene-oxazoline (0.8 g, 3 mmol) was dissolved in 50 mL of toluene under nitrogen.2,6-Dimethylaniline (436.2 mg, 3.6 mmol), Pd(OAc) 2 (34 mg, 0.15 mmol), rac-BINAP (93 mg, 0.15 mmol),Sodium tert-butoxide (470.4 mg, 4.2 mmol), heated to reflux for 48 h, cooled and filtered.With NaHCO3 solution (2 × 200mL)Wash with water (2 x 100 mL),concentrate,Column chromatographyThe product was purified (573.7 mg, 62.0%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: thionyl chloride / 12 h / Reflux 2: triethylamine / dichloromethane / 12 h / 0 - 20 °C 3: thionyl chloride / dichloromethane / 4 h / 0 - 64 °C 4: water; sodium hydroxide / methanol / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: thionyl chloride / dichloromethane / 4 h / 0 - 64 °C 2: water; sodium hydroxide / methanol / 4 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.5% | With water; sodium hydroxide In methanol for 4h; Reflux; |
A280412[ 148836-24-2 ]
(S)-2-(2-Bromophenyl)-4-isopropyl-4,5-dihydrooxazole
Reason: Optical isomers
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