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Product Details of 6-Bromo-3,4-dihydro-1(2H)-naphthalenone

CAS No. :66361-67-9
Formula : C10H9BrO
M.W : 225.08
SMILES Code : O=C1CCCC2=C1C=CC(Br)=C2
MDL No. :MFCD04114378
InChI Key :OSDHOOBPMBLALZ-UHFFFAOYSA-N
Pubchem ID :10105069

Safety of 6-Bromo-3,4-dihydro-1(2H)-naphthalenone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of 6-Bromo-3,4-dihydro-1(2H)-naphthalenone

* 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 [ 66361-67-9 ]

[ 66361-67-9 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 66361-67-9 ]
  • [ 1415108-26-7 ]
  • 2
  • [ 823-96-1 ]
  • [ 66361-67-9 ]
  • [ 51015-29-3 ]
YieldReaction ConditionsOperation in experiment
91% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 105℃;Inert atmosphere; 6.24. Synthetic Method TPreparation of 6-Methyl-3,4-dihydronaphthalen-1(2H)-one (4a); Under N2, bromide 68 (1.00 g, 4.44 mmol), Pd(PPh3)4 (0.796 g, 0.689 mol), and K2CO3 (1.84 g, 13.3 mmol) were suspended in DMF (10 mL). Trimethylboroxine (1.26 g, 10.0 mmol) was added dropwise via syringe at room temperature, then the reaction was heated at 105 C. overnight. The crude reaction was cooled to room temperature, diluted with DCM (50 mL), washed with H2O (3×), brine solution, dried over MgSO4 and concentrated in vacuo. The crude oil was purified by silica gel chromatography (ethyl acetate-hexanes gradient) to give ketone 69 (0.648 g, 91% yield) as a clear oil.
  • 3
  • [ 13061-96-6 ]
  • [ 66361-67-9 ]
  • [ 51015-29-3 ]
YieldReaction ConditionsOperation in experiment
88% With potassium phosphate; palladium diacetate; triphenylphosphine; In tetrahydrofuran;Inert atmosphere; Reflux; A solution of 19 (1.4 g, 6.1 mmol), methyl boronic acid (0.6 g, 9.3 mmol), Pd(OAc)2 (0.07 g, 0.31 mmol), PPh3 (0.16 g, 0.61 mmol), and K3PO4 (5.2 g, 24 mmol) in dry THF were stirred at reflux under N2 atm overnight. After cooling at room temperature, crude was filtered through celite, concentrated by rotary evaporation, and purified by column chromatography to give 6-methyl-3,4-dihydronaphthalen-1(2H)-one (20) (88%). 1H NMR (600 MHz, CDCl3) delta 7.93 (d, J=12.0 Hz, 1H), 7.11 (d, J=12.0 Hz, 1H), 7.06 (s, 1H), 2.92 (t, J=6.0 Hz, 2H), 2.63 (t, J=12.0 Hz, 2H), 2.37 (s, 3H), 2.13-2.10 (m, 2H). GC-MS (ES) for C11H12O [M]+ 160
  • 4
  • [ 19936-14-2 ]
  • [ 66361-67-9 ]
YieldReaction ConditionsOperation in experiment
55% With copper; potassium carbonate; Selectfluor; In water; acetonitrile; at 80℃; for 2h; 1-(4-bromophenyl) butanol, 0.4mmolSelectfluor, 0 . 02mmolCu powder, 0.2mmolK 2 CO 3 added to 10 ml in the reaction pipe, then adding 2mLCH 3 CN:H 2 O (V:V= 150:1) as a solvent. Furthermore, for 80 C magnetic stirring under the conditions of 2h. Furthermore, by adding the reaction liquid chromatographic silica gel spoon column the two drugs (100-200 mesh), and by reduced pressure distillation to remove the solvent, the product obtained by separation column chromatography pure product (with petroleum ether/acetic acid ethyl ester volume ratio = 6:1 as the eluant). The material is the yellow solid, yield 55%. Characterization data: mp:44-45 C; 1 HNMR (400MHz, CDCl 3): delta 7.89 (d, J = 8.9Hz, 1H), 7.46 7.44 (m, 2H), 2.94 (t, J = 6.2Hz, 2H), 2.65 (t, J = 6.6Hz, 2H), 2.14 (m, 2H).
 

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• Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

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