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Chemical Structure| 57455-06-8 Chemical Structure| 57455-06-8

Structure of 3-Iodobenzyl alcohol
CAS No.: 57455-06-8

Chemical Structure| 57455-06-8

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Product Details of [ 57455-06-8 ]

CAS No. :57455-06-8
Formula : C7H7IO
M.W : 234.03
SMILES Code : OCC1=CC=CC(I)=C1
MDL No. :MFCD00004635
InChI Key :QGCCNWSXJHGUNL-UHFFFAOYSA-N
Pubchem ID :42300

Safety of [ 57455-06-8 ]

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

Application In Synthesis of [ 57455-06-8 ]

* 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 [ 57455-06-8 ]

[ 57455-06-8 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 57455-06-8 ]
  • [ 60076-09-7 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; In dichloromethane; at 20℃; for 30h;Reflux; A solution of 3-iodobenzyi alcohol (600 mg, 2.56 mmol) in DCM (3ml) was treated with thionyl chloride (3 ml, 41.3 mmol) and stirred at ambient temperature for 18h, before addition of further thionyl chloride (1 ml, 13.7 mmol) and heating to reflux for 12h. The cooled solution was basified with 50% NaOH, diluted with water and extracted with DCM, The combined organics were dried over MgS04, filtered and evaporated to afford a clear syrup which crystallises on standing to give 3-iodobenzyl chloride as a white solid (650mg, quant.).
With thionyl chloride; In toluene; at 60 - 90℃; for 4h; Reference example 15-1 Preparation for dimethyl (3-iodobenzyl)malonate To a solution of m-iodobenzylalcohol (5.0g, 21.4mmol) in toluene (60ml) was added thionyl chloride (5.5g, 46.2mmol), and the mixture was stirred for 2 hours at 60C. Additional thionyl chloride (3.5g, 29.4mmol) was added thereto and the mixture was further stirred for 2 hours at 90C. The reaction mixture was concentrated under reduced pressure to give a mixture of m-iodobenzyl chloride. To a solution of dimethyl malonate (2.3g, 17.4mmol) in methanol (20ml) was added sodium methoxide/methanol (28%, 3.3g, 17.4mmol), and the mixture was stirred for 2 hours at 60 C. Thereto was added the mixture of m-iodobenzyl chloride in tetrahydrofuran (50ml) at 60C and the mixture was stirred for 2 hours at 60C and for 90 hours at room temperature. The solvent was removed and the residue was diluted with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried over magnesium sulfate. The solvent was removed and the residue was purified with silica gel chromatography (hexane:ethyl acetate=8:1→2:1) to give the subject compound (0.98g, 16%).1H NMR (CDCl3, 400 MHz) δ 7.54 - 7.58 (m, 2 H), 7.17 (brd, 1 H, J = 7.9 Hz), 7.02 (brt, 1 H, J = 7.9 Hz), 3.71 (s, 6 H), 3.63 (t, 1 H, J = 7.8 Hz), 3.15 (d, 2 H, J = 7.8 Hz).
With methanesulfonyl chloride; triethylamine; In dichloromethane; at 20℃; for 2h; Methanesulfonylchloride (868 pL, 10.7 mmol) is added to a stirred solution of 3-lodo- benzyl alcohol (2.5 g, 11.2 mmol) and triethylamine (3.7 ml, 26.7 mmol) dissolved in dry DCM and the reaction mixture is stirred at room temperature for 2 hours. Water is added, the organic layer is separated and concentrated under reduced pressure toobtain the crude title compound (yield 2.5 g).GO (Method 9): tR = 7.91 mm; Mass spectrum (Eli-): mlz = 252 [M]
  • 2
  • [ 874483-75-7 ]
  • [ 57455-06-8 ]
  • [ 60076-09-7 ]
  • 3
  • [ 5918-93-4 ]
  • [ 57455-06-8 ]
  • 4-(3-(hydroxymethyl)phenyl)-1H-imidazol-2(3H)-one [ No CAS ]
  • 4
  • [ 57455-06-8 ]
  • [ 603-33-8 ]
  • [ 69605-90-9 ]
YieldReaction ConditionsOperation in experiment
81% With tetrabutylammomium bromide; potassium acetate; palladium diacetate; tris-(o-tolyl)phosphine; In 1-methyl-pyrrolidin-2-one; at 110℃; for 4h;Schlenk technique; Inert atmosphere; General procedure: Cross-coupling of 1a with Bi(p-tolyl) 3 : An oven-dried Schlenk tube was charged with (2-iodophenyl)methanol (1a) (0.75 mmol, 3 equiv.), Bi(p-tolyl) 3 (0.25 mmol, 1 equiv.), Pd(OAc) 2 (0.025 mmol, 0.1 equiv.), P(o-tolyl) 3 (0.1 mmol, 0.4 equiv.), KOAc(1.5 mmol, 6 equiv.), TBAB (0.75 mmol, 3 equiv.) and NMP (3 mL) under a N 2atmosphere. The mixture was stirred in an oil bath at 110 C for 4 h. The contents were quenched with water (10 mL) at rt and extracted with ethylacetate (30 mL). The organic extract was washed with brine and dried usingMgSO 4 . The organic solvent was removed under reduced pressure to obtain thecrude product. It was puried by silica gel chromatography using hexane/ethylacetate as eluent. The product 2a was obtained in 74% yield. The spectralcharacterization data for all the products is given in the Supporting information.
 

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