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[ CAS No. 66826-78-6 ]

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Chemical Structure| 66826-78-6
Chemical Structure| 66826-78-6
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Product Details of [ 66826-78-6 ]

CAS No. :66826-78-6 MDL No. :MFCD02677716
Formula : C8H7BrO Boiling Point : 251.658°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :199.04 g/mol Pubchem ID :2776159
Synonyms :

Safety of [ 66826-78-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H312-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66826-78-6 ]

  • Upstream synthesis route of [ 66826-78-6 ]
  • Downstream synthetic route of [ 66826-78-6 ]

[ 66826-78-6 ] Synthesis Path-Upstream   1~16

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Reference: [1] Heterocycles, 1997, vol. 45, # 9, p. 1657 - 1661
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YieldReaction ConditionsOperation in experiment
70.3% With bromine In 1,4-dioxane; ethyl acetate Preparation 94
To an ice-cooled dioxane (30 ml) was slowly added liquid bromine (2.66 g) and this mixture was stirred for 30 minutes at said temperature.
To the mixture was added dropwise 2,3-dihydrobenzofuran (2 g), and the resulting mixture was stirred for 3 hours at room temperature.
The solvent was removed under reduced pressure.
The residue was dissolved in AcOEt (50 ml) and the solution was washed with saturated aqueous NaHCO3 solution and brine, and dried over MgSO4.
The solvent was evaporated to give an orange oil as a crude product.
The crude product was purified on an SiO2 column (hexane-AcOEt 20:1) to give 2.33 g of 5-bromo-2,3 dihydrobenzofuran as white crystals (yield 70.3percent).
1H-NMR (300 MHz, CDCl3, δ): 3.11(2H, t, J=11 Hz), 4.57(2H, t, J=11 Hz), 6.66(1H, d, J=8 Hz), 7.20(1H, d, J=8 Hz), 7.30(1H, s)
28% at 10℃; for 1.16667 h; To a chilled (10°C) solution of 10 g (83 mmol) of 2, 3-dihydrobenzofuran in 50 mL of acetic acid, 4 mL (78 mmol) of bromine in 6 mL of acetic acid was added dropwise over a 10 minute period. After 1 hour, the mixture was made basic by cautiously pouring the reaction mixture into saturated/solid aqueous sodium bicarbonate and stirring overnight. The mixture was then extracted with three 100 mL portions of EtOAc. The combined organic layers were washed with two 50 mL portions of saturated aqueous sodium bicarbonate, three 50 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated to afford a yellow oil. The oil was diluted with hexane and passed through a pad (600 mL funnel) of silica gel eluting with hexane to afford a white solid which was diluted with cold (dry ice-acetone) hexane and collected by filtration to afford 4.7 g (28percent) of the title compound as a white solid, m. p. 45°C- 48°C. The filtrate was concentrated to afford 5.1 g of 5-bromo-2, 3-dihydrobenzofuran which was 70percent pure.
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336
[2] Chemistry - A European Journal, 2017, vol. 23, # 5, p. 1044 - 1047
[3] Synthesis, 1988, # 12, p. 950 - 952
[4] Patent: US6333324, 2001, B1,
[5] Patent: WO2003/82787, 2003, A1, . Location in patent: Page/Page column 137-138
[6] Synlett, 2005, # 18, p. 2837 - 2842
[7] Patent: US6235771, 2001, B1,
[8] Patent: WO2007/27917, 2007, A2, . Location in patent: Page/Page column 23-25
[9] Patent: EP1394147, 2004, A1, . Location in patent: Page 92
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Reference: [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 7, p. 1384 - 1388
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Reference: [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360
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Reference: [1] Organic Letters, 2001, vol. 3, # 21, p. 3357 - 3360
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Reference: [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163
[2] Journal of the American Chemical Society, 1920, vol. 42, p. 163
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Reference: [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163
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Reference: [1] Journal of the American Chemical Society, 1920, vol. 42, p. 163
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 7, p. 1384 - 1388
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Reference: [1] Synthesis, 1988, # 12, p. 950 - 952
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Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 16, p. 4313 - 4336
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Reference: [1] Patent: US6649643, 2003, B1,
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Reference: [1] Synthesis, 1988, # 12, p. 950 - 952
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Reference: [1] Angewandte Chemie - International Edition, 2008, vol. 47, # 6, p. 1115 - 1118
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Reference: [1] Patent: US6387931, 2002, B1,
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