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Chemical Structure| 452-09-5
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Product Details of [ 452-09-5 ]

CAS No. :452-09-5
Formula : C7H6ClFO
M.W : 160.57
SMILES Code : COC1=CC=C(Cl)C=C1F
MDL No. :MFCD00672964
InChI Key :QIUCVZDNIUACJN-UHFFFAOYSA-N
Pubchem ID :223101

Safety of [ 452-09-5 ]

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

Application In Synthesis of [ 452-09-5 ]

* 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.

  • Upstream synthesis route of [ 452-09-5 ]

[ 452-09-5 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 452-09-5 ]
  • [ 867333-04-8 ]
YieldReaction ConditionsOperation in experiment
39%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333 h;
Stage #2: With Trimethyl borate In tetrahydrofuran at -78 - 20℃; for 2 h;
Stage #3: With hydrogenchloride; water In tetrahydrofuran
2.5M nBuLi (14.9 mL, 37.4 mmol) was added dropwise over 5 minutes into a mixture of 4-chloro-2-fluoro-1-methoxybenzene (5 g, 31.1 mmol) in anhydrous THF (30 mL) at -78° C.
After the mixture was stirred at -78° C. for 20 minutes, anhydrous trimethyl borate (4.9 g, 46.6 mmol) was added into the solution at -78° C.
The reaction mixture was brought to room temperature for over period of 2 h.
The reaction was quenched by 2N HCl (1 mL).
THF was removed by vacuum.
The crude product was diluted with 2N HCl (100 mL).
The acidic solution was extracted with ethyl acetate (2*50 mL).
The combined ethyl acetate fraction was dried over sodium sulfate.
The sodium sulfate was removed by filtration and the solvent was removed by vacuum.
The oil was titrated with hexanes/chloroform (1:1) to yield a solid.
The precipitate was collected by filtration and washed with hexanes to yield a white solid (2.5 g, 39percent).
1H NMR DMSO-d6: δ 3.81 (s, 3H), 7.12 (m, 2H), 8.66 (s, 2H).
References: [1] Patent: US2005/245524, 2005, A1, . Location in patent: Page/Page column 97.
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  • [ 452-09-5 ]
  • [ 867333-04-8 ]
References: [1] Organic Process Research and Development, 2014, vol. 18, # 10, p. 1211 - 1220.
 

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