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Chemical Structure| 689290-84-4 Chemical Structure| 689290-84-4

Structure of 689290-84-4

Chemical Structure| 689290-84-4

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Product Details of [ 689290-84-4 ]

CAS No. :689290-84-4
Formula : C11H8BrCl
M.W : 255.54
SMILES Code : ClCC1=CC2=CC=C(Br)C=C2C=C1
English Name :2-Bromo-6-(chloromethyl)naphthalene
MDL No. :MFCD09842472

Safety of [ 689290-84-4 ]

Application In Synthesis of [ 689290-84-4 ]

* 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 [ 689290-84-4 ]

[ 689290-84-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 100751-63-1 ]
  • [ 689290-84-4 ]
YieldReaction ConditionsOperation in experiment
99% With thionyl chloride; zinc(II) chloride In 1,4-dioxane at -10℃;
99% With thionyl chloride In 1,4-dioxane at 20 - 40℃; for 2h; 1.1B Example 1B2-bromo-6-(chloromethyl)naphthalene A stirred solution of the product from Example 1A (30.5 g, 129 mmol) in dioxane (320 ML) under a dry nitrogen atmosphere was chilled to 40° C. Solid anhydrous ZnCl2 (514 mg, 3.77 mmol, 0.03 equiv.) was added in one lot, followed by the dropwise addition of thionyl chloride (19.3 ML, 264 mmol, 2.0 equiv.).The reaction mixture was allowed to warm to room temperature then stirred an additional 2 hr.This reaction mixture was then concentrated under reduced pressure and the residue was partitioned between dichloromethane and saturated aqueous NaHCO3 (500 ML).The organic layer was washed with brine (2*100 ML), dried (MgSO4), and filtered.The filtrate was concentrated under reduced pressure to give a white solid.Drying under vacuum overnight at 40° C. provided the product (32.6 g, 99% yield). M.p. 133.1-134.1° C. h NMR (CDCl3, 300 MHz) δ 8.00 (d, J=2 Hz, 1H), 7.81-7.67 (m, 3H), 7.56 (dd, J=2, 12 Hz, 1H), 7.54 (dd, J=2, 12 Hz, 1H), 4.73 (s, 2H). MS (DCl-NH3) [M+NH4-H2O]+ at 254.
98% With thionyl chloride; zinc(II) chloride In 1,2-dimethoxyethane at 0 - 20℃;
96% With thionyl chloride; zinc(II) chloride In 1,2-dimethoxyethane at 5 - 25℃; Inert atmosphere; Large scale;
92% With thionyl chloride; zinc(II) chloride In dichloromethane at -5 - 20℃; LXI To a solution of compound LXI-2 (39.0g, 164.6 mmoml) and ZnCl2 (0.4 lg, 3.1 mmoml) in DCM (600 mL) was added SOCl2 (39.0g, 329.2 mmol) at -5 °C. The mixture was stirred for overnight at room temperature and then concentrated to get residue and washed with heptane at -10 °C to get compound LXI-3 (38.5g, yield: 92.0%).
75% With thionyl chloride In acetonitrile at 0 - 20℃; for 1h; 103 Preparation Example 103: 2-bromo-6-chloromethyl-naphthalene (6-bromo-naphthalen-2-yl)-methanol (0.307 g, 1.29 mmol) obtained in Preparation Example 102 was dissolvedin 5 mL of acetonitrile. Thionyl-chloride (0.188 mL, 2.59 mmol) was added thereto at 0°C, and the mixture was stirredat room temperature for 1 hour. The reaction solution was distilled under reduced pressure and purified by columnchromatography to obtain the title compound (0.248 g, 75%).1H-NMR (CDCl3) δ 8.00 (1H, s), 7.83-7.68 (3H, m), 7.58-7.53 (2H, m), 4.73 (2H, s).
With thionyl chloride; zinc(II) chloride In 1,4-dioxane for 0.666667h;

 

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