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[ CAS No. 69626-75-1 ]

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Chemical Structure| 69626-75-1
Chemical Structure| 69626-75-1
Structure of 69626-75-1 * Storage: {[proInfo.prStorage]}

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Product Details of [ 69626-75-1 ]

CAS No. :69626-75-1 MDL No. :MFCD18451197
Formula : C8H5IO Boiling Point : -
Linear Structure Formula :- InChI Key :N/A
M.W :244.03 g/mol Pubchem ID :-
Synonyms :

Safety of [ 69626-75-1 ]

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

Application In Synthesis of [ 69626-75-1 ]

  • Downstream synthetic route of [ 69626-75-1 ]

[ 69626-75-1 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 271-89-6 ]
  • [ 69626-75-1 ]
YieldReaction ConditionsOperation in experiment
82% General procedure: To a stirred, cooled (0 C) solution of 2,2,6,6-tetramethylpiperidine (0.25 mL, 1.5 mmol) in THF (2-3 mL) were successively added BuLi (about 1.6 M hexanes solution, 1.5 mmol) and, 5 min later, ZnCl2?TMEDA14 (0.13 g, 0.50 mmol). The mixture was stirred for 15 min at 0 C before introduction of the substrate (1.0 mmol) at 0-10 C. After 2 h at room temperature, a solution of I2 (0.38 g,1.5 mmol) in THF (4 mL) was added. The mixture was stirred overnight before addition of an aqueous saturated solution of Na2S2O3(4 mL) and extraction with AcOEt (3 20 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. To the crude iodide were added Cs2CO3(0.65 g, 2.0 mmol), Cu powder (13 mg, 0.20 mmol), the azole (1.5 mmol) and MeCN (5 mL) and the resulting mixture was heated under reflux for 24 h. Filtration over Celite, washing with AcOEt,removal of the solvent and purification by chromatography on silica gel (the eluent is given in the product description) led to the compound described below.
80% To a solution of benzofiiran (466 muL, 4.2 mmol) in THF (15 mL) was added t-BuLi (1.7 M, 2.73 mL, 1.1 eq.) at -780C (Scheme 11). After stirring at the same temperature for 30 minutes, a solution of h (1.180 g, 1.1 eq.) in THF (5 mL) was added dropwise. The mixture was warmed up gradually to room temperature and stirred for 1.5 hours. The reaction was diluted with ethyl acetate (20 mL). Excess I2 was reduced with 10% Na2S2theta7 solution. The organic layer was washed with brine (2 x 10 mL), dried (MgSO4) and concentrated under reduced pressure. Purification by flash column chromatography afforded 60 (0.826 g, 80%) as yellow-orange liquid. 1H NMR (CDCl3): 6.96 (s, IH), 7.18-7.24 (m, 2H), 7.46-7.52) (m, 2H).
To a solution of benzofuran (3.0 g, 25.4 mmol) in tetrahydrofuran (36 mL) at about- 78 C was added a 2. 5M solution of n-butyllithium in hexanes (10.2 mL, 25.4 mmol). The solution was allowed to warm to about-10 C and was stirred for about 2 hours. Iodine (6.41 g, 25.4 mmol) was added gradually and the mixture was stirred at about-10 C for about 30 min. The solution was allowed to warm to room temperature, was quenched by the addition of aqueous ammonium chloride, and was extracted with diethyl ether. The combined organic extracts were washed with aqueous sodium bisulfite and brine, dried (MgS04), filtered and concentrated under vacuum. The resulting oil was distilled (b. p. 90 C/1. 05 mm Hg) to provide Example 651. in NMR (300 MHz, CDC13) : 8 6.93 (s, 1H), 7.20 (m, 2H), 7. 48 (m, 2H)
  • 2
  • [ 69626-75-1 ]
  • [ 4301-14-8 ]
  • [ 39165-03-2 ]
YieldReaction ConditionsOperation in experiment
72% With tetrakis(triphenylphosphine) palladium(0); zinc dibromide In tetrahydrofuran at 22 - 23℃; for 1h;
  • 3
  • [ 917-64-6 ]
  • [ 69626-75-1 ]
  • [ 23619-59-2 ]
  • [ 6395-29-5 ]
YieldReaction ConditionsOperation in experiment
1: 46% 2: 18% With manganese(ll) chloride In diethyl ether for 28h; Heating;
  • 4
  • phenylmagnesium bromide [ No CAS ]
  • [ 69626-75-1 ]
  • [ 18493-15-7 ]
YieldReaction ConditionsOperation in experiment
62% With manganese(ll) chloride In diethyl ether for 16h; Heating;
  • 5
  • [ 69626-75-1 ]
  • [ 85960-75-4 ]
YieldReaction ConditionsOperation in experiment
88% With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 2h;
  • 6
  • [ 69626-75-1 ]
  • [ 138118-26-0 ]
YieldReaction ConditionsOperation in experiment
85% With manganese(ll) chloride In diethyl ether at 0 - 25℃;
  • 7
  • [ 69626-75-1 ]
  • ((E)-2-Penta-1,4-dienyl)-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
46% With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 3.5h;
  • 8
  • [ 69626-75-1 ]
  • [ 138118-26-0 ]
YieldReaction ConditionsOperation in experiment
49% Stage #1: 2-iodobenzofuran; n-Bu3MnMgBr In tetrahydrofuran at 0 - 50℃; for 3h; Stage #2: With hydrogenchloride In tetrahydrofuran
  • 9
  • [ 69626-75-1 ]
  • C12H15(2)HO [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% Stage #1: 2-iodobenzofuran; n-BuMgBr With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 3h; Stage #2: With water-d2 In tetrahydrofuran
  • 10
  • [ 69626-75-1 ]
  • [ 106-95-6 ]
  • 2-(2-butyl-penta-1,4-dienyl)-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% Stage #1: 2-iodobenzofuran; n-BuMgBr With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 1.5h; Stage #2: allyl bromide In diethyl ether at 0 - 25℃; for 1.5h;
  • 11
  • [ 100-52-7 ]
  • [ 69626-75-1 ]
  • 2-[(Z)-2-(Hydroxy-phenyl-methyl)-hex-1-enyl]-phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% Stage #1: 2-iodobenzofuran; n-BuMgBr With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 1.5h; Stage #2: benzaldehyde In diethyl ether at 0 - 25℃; for 1.5h;
  • 12
  • [ 124-38-9 ]
  • [ 69626-75-1 ]
  • [ 66898-41-7 ]
YieldReaction ConditionsOperation in experiment
53% Stage #1: 2-iodobenzofuran; n-BuMgBr With manganese(ll) chloride In diethyl ether at 0 - 25℃; for 1.5h; Stage #2: carbon dioxide In diethyl ether at -78 - 25℃; for 0.5h;
  • 13
  • diethyl 2-(2-cyclohepten-1-yl)-2-(2-propynyl)malonate [ No CAS ]
  • [ 69626-75-1 ]
  • diethyl 2-[3-(1-benzofuran-2-yl)-2-propynyl]-2-(2-cyclohepten-1-yl)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃;
  • 14
  • [ 69626-75-1 ]
  • Acetic acid (2R,4S)-2-phenethyl-3,4-dihydro-2H-pyran-4-yl ester [ No CAS ]
  • 2-(6-phenethyl-5,6-dihydro-2<i>H</i>-pyran-2-yl)-benzofuran [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% Stage #1: 2-iodobenzofuran With tert.-butyl lithium In diethyl ether; pentane at -78℃; Stage #2: With zinc(II) chloride In diethyl ether; pentane at -78℃; Stage #3: Acetic acid (2R,4S)-2-phenethyl-3,4-dihydro-2H-pyran-4-yl ester In diethyl ether; pentane at 25℃; Further stages.;
  • 15
  • [ 918-86-5 ]
  • [ 69626-75-1 ]
  • (E)-3-Benzofuran-2-ylmethyl-pent-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tetraethylammonium chloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 120℃; for 6.5h;
Historical Records

Related Functional Groups of
[ 69626-75-1 ]

Iodides

Chemical Structure| 112768-48-6

[ 112768-48-6 ]

2-Iodobenzofuran-6-ol

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Related Parent Nucleus of
[ 69626-75-1 ]

Benzofurans

Chemical Structure| 112768-48-6

[ 112768-48-6 ]

2-Iodobenzofuran-6-ol

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