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[ CAS No. 67159-88-0 ]

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Chemical Structure| 67159-88-0
Chemical Structure| 67159-88-0
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Product Details of [ 67159-88-0 ]

CAS No. :67159-88-0 MDL No. :MFCD26403409
Formula : C11H13Br Boiling Point : -
Linear Structure Formula :- InChI Key :CC1(C)CCC2=C1C=C(Br)C=C2
M.W :225.13 g/mol Pubchem ID :-
Synonyms :

Safety of [ 67159-88-0 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 67159-88-0 ]

  • Upstream synthesis route of [ 67159-88-0 ]
  • Downstream synthetic route of [ 67159-88-0 ]

[ 67159-88-0 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 67159-88-0 ]
  • [ 67159-85-7 ]
YieldReaction ConditionsOperation in experiment
82.3% With tert.-butylhydroperoxide In dichloromethane at 20℃; Sealed system Step 1 5-Bromo-3,3-dimethyl-indan-1-one; 6-Bromo-1,1-dimethyl-indan 8g (4g, 17.8 mmol) was dissolved in 40 mL of anhydrous dichloromethane, followed by addition of chromium oxide (280 mg, 1.8 mmol) and slowly dropwise addition of tert-butyl hydroperoxide (19 mL, 190 mmol). The reaction system was sealed and stirred overnight at room temperature after the reaction solution was crimson and the generated gas was released. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was diluted with 50 mL of water and extracted with dichloromethane (100 mL.x.3). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-bromo-3,3-dimethyl-indan-1-one 19a (3.5 g, 82.3percent) as a white solid. MS m/z (ESI): 238 [M-1]
76% at 60℃; for 3 h; To a solution of 6-bromo-1,1-dimethyl-2,3-dihydro-1H-indene (3.6 g, 16 mmol) in acetic acid (50 mL) was added to a solution of CrO3 (9.6 g, 96.0 mmol) in 50percent aqueous acetic acid (50 mL). This solution was heated for 3 h at 60° C. At completion, the reaction mixture was quenched by the addition of isopropanol (20 mL). The quenched reaction was partitioned between EtOAc (200 mL) and a 0.25 M aqueous NaOH (100 mL). The layers were separated and the organics were extracted with EtOAc (2.x.100 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. After purification by flash chromatography over silica gel (50percent EtOAc/hexanes eluent), 5-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one (2.91 g, 76percent yield) was isolated as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.65 (s, 1H), 7.47-7.58 (m, 2H), 2.58 (s, 2H), 1.42 (s, 6H); MS (EI) m/z=240.1 [M+1]+.
37% at 55℃; for 0.5 h; To a solution of the title compound from Step A above (2.10 g) in acetic acid was added a solution of CrO3 (3.72 g) in 50percent aqueous acetic acid (20 mL) at 55° C. and the mixture was stirred for 30 min at this temperature. After cooling to 0° C. 2-propanol (5 mL) was added and the mixture was diluted with ethyl acetate (400 mL), washed with 0.5M sodium hydroxide and brine, dried (MgSO4), concentrated and purified by column chromatography (silica, cyclohexane/EtOAc, 9:1) to afford the title compound (829 mg; 37percent) as an oil. [MH]+=239/241.
Reference: [1] Patent: EP2236500, 2010, A1, . Location in patent: Page/Page column 39-40
[2] Patent: US2012/225857, 2012, A1, . Location in patent: Page/Page column 24
[3] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 123
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