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Chemical Structure| 1104637-62-8 Chemical Structure| 1104637-62-8

Structure of 1104637-62-8

Chemical Structure| 1104637-62-8

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Product Details of [ 1104637-62-8 ]

CAS No. :1104637-62-8
Formula : C9H10BNO5
M.W : 222.99
SMILES Code : O=C(CN(C)C1)OB(C2=CC=CO2)OC1=O
MDL No. :MFCD11215213

Safety of [ 1104637-62-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1104637-62-8 ]

* 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 [ 1104637-62-8 ]

[ 1104637-62-8 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1104637-62-8 ]
  • [ 18995-35-2 ]
  • [ 1158984-98-5 ]
YieldReaction ConditionsOperation in experiment
94% Under ambient atmosphere, to a 40 mL I-Chem vial equipped with a stir bar was added 1 -te/t-butoxy-4-chlorobenzene (3a) (185 mg, 1.00 mmol), the MIDA boronate or freshly-prepared boronic acid (1.00 mmol), 2-dicyclohexylphosphino-2',6'- dimethoxybiphenyl (SPhos) (41 mg, 0.10 mmol) and Pd(OAc)2 (1 1 mg, 0.050 mmol). The vial was sealed with a PTFE-lined septum screw-cap and was placed under Ar atmosphere. To the vial was added dioxane (12.5 mL) and the resulting mixture was stirred at 23 0C for 10 min. To the vial was then added aqueous K3PO4 (3.0 M, 2.5 mL, degassed by sparging with Ar for 30 min). The vial was placed in a 60 0C oil bath with stirring for 6 h. After cooling to room temperature the mixture was transferred to a 60 mL separatory funnel and was diluted with aqueous NaOH (1.0 M, 10 mL) and Et2O (10 mL). The mixture was shaken and the phases were separated. The aqueous phase was extracted with Et2O (3 x 10 mL). The combined organic fractions were dried over MgSO4, filtered and concentrated in vacuo. The crude residue was subjected to flash- chromatography on silica gel (hexanes:EtOAc). This method is depicted in the scheme below, and the yields of cross-coupling are listed in FIG. 2. To form 2-(4-te/t-butoxyphenyl)furan (4a), the general procedure was followed using MIDA boronate 2a (223 mg, 1.00 mmol) to afford 4a as a colorless oil (203 mg, 94%). A parallel reaction using freshly-prepared boronic acid 1a (1 12 mg, 1.00 mmol) under otherwise identical conditions afforded 4a as a colorless oil (147 mg, 68%). TLC (hexanes:EtOAc 20:1) Rf = 0.33, visualized by UV (254 nm). 1H-NMR (500 MHz, CDCI3) δ 7.60 (d, / = 8.5 Hz, 2H), 7.45 (dd, / = 1.5, 0.5 Hz, 1 H), 7.04 (d, / = 8.5 Hz, 2H), 6.58 (d, / = 3.0 Hz, 1 H), 6.46 (dd, / = 3.0, 1.5 Hz, 1 H), 1.38 (s, 9H). 13C-NMR (125 MHz, CDCl3) δ 154.8, 153.9, 141.6, 126.3, 124.4, 124.3, 1 1 1.5, 104.0, 78.7, 28.8. HRMS (Cl +) Calculated for C14H16O2 (M) + : 216.1150, Found: 216.1 151 . IR (thin film, cm-1) 2977, 1612, 1587, 1566, 1512, 1481 , 1414, 1390, 1366, 1245, 1 162, 1 106, 1078, 1007, 904, 895, 854, 798, 730, 667, 594.
 

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