[ CAS No. 1155371-47-3 ]

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CAS No. 1155371-47-3, is an aryls compound, with a molecular weight of 306.14, molecular formula C11H15IO2, Ambeed provides reports for batches of (such as NMR, HPLC/GC).

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Product Details

CAS No. :1155371-47-3MDL No. :N/A
Formula :C11H15IO2InChI Key :QBTLWHYKYLZHKG-UHFFFAOYSA-N
M.W :306.14Pubchem ID :68900806
Boiling Point :-
Synonyms :

Computed Properties

TPSA : 18.5 H-Bond Acceptor Count : 2
XLogP3 : 3.6 H-Bond Donor Count : 0
SP3 : 0.45 Rotatable Bond Count : 3

Safety

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis

[ 1155371-47-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1155371-47-3 ]
  • [ 1066-54-2 ]
  • [ 1155371-48-4 ]
YieldReaction ConditionsOperation in experiment
70% Heating / reflux A suspension of 1-iodo-5-isopropyl-2,4-dimethoxybenzene (344 mg, 1.12 mmol) in freshly distilled Et3N in a screwcap vial was added Pd(PPh3)2CI2 (48 mg), CuI (68 mg, 0.36 mmol), and trimethylsilyiacetylene (0.8 ml, 5.66 mmol). The mixture was stirred at reflux overnight. The vial was then cooled to room temperature and the reaction mixture diluted with diethylether, and the organic phase was washed with a saturated solution of NH4CI and then with a saturated solution of NaHCO3. The organic phase was dried (MgSO4) and evaporated. The residue was purified by column chromatography using 5percent EtOAc in petrol ether as eluent. The title compound (219 mg, 70percent) was isolated as a solid. NMR (DMSO-c/e): δ 7.09 (s, 1 H), 6.61 (s, 1 H), 3.85 (s, 3H), 3.83 (s, 3H), 3.11 (m, 1 H), 1.11 (d, 6H), 0.198 (s, 9H).
Reference: [1] Patent: WO2009/66060, 2009, A2. Location in patent: Page/Page column 100; 103

[ 1155371-47-3 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1155371-46-2 ]
  • [ 1155371-47-3 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With tert.-butyl lithium In diethyl ether at -78℃; for 0.75 h;
Stage #2: With iodine In diethyl ether at -78 - 20℃; for 1.00 h;
A solution of 1-bromo-5-isopropyl-2,4-dimethoxybenzene (0.396 g, 1.53 mmol) in dry diethylether (3 mL) was cooled to -78°C. t-Bul\\ (1 mL, 1.7 M) was added dropwise and the mixture stirred at -78°C for 45 minutes. A solution of I2 (0.391 g, 1.54 mmol) in ether (3 mL) was added in one portion and the temperature maintained at -780C for 1 hour, and then heated to room temperature. The reaction mixture was washed with a solution of 25percent NaS2O3 to remove excess iodine. The organic phase was isolated, dried (MgSO4), and evaporated. The residue was purified by column chromatography using 10percent EtOAc in heptane as eluent. The title compound (0.249 g, 53percent) was isolated as a white solid. NMR (DMSO-CZ6): δ 7.41 (s, 1 H), 6.64 (s, 1 H), 3.76 (s, 3H), 3.72 (s, 3H), 3.10 (m, 1H), 1.11 (d, 6H).
Reference: [1] Patent: WO2009/66060, 2009, A2. Location in patent: Page/Page column 100; 102
  • 2
  • [ 1155371-46-2 ]
  • [ 1155371-47-3 ]
YieldReaction ConditionsOperation in experiment
53%
Stage #1: With tert.-butyl lithium In diethyl ether at -78℃; for 0.75 h;
Stage #2: With iodine In diethyl ether at -78 - 20℃; for 1.00 h;
A solution of 1-bromo-5-isopropyl-2,4-dimethoxybenzene (0.396 g, 1.53 mmol) in dry diethylether (3 mL) was cooled to -78°C. t-Bul\\ (1 mL, 1.7 M) was added dropwise and the mixture stirred at -78°C for 45 minutes. A solution of I2 (0.391 g, 1.54 mmol) in ether (3 mL) was added in one portion and the temperature maintained at -780C for 1 hour, and then heated to room temperature. The reaction mixture was washed with a solution of 25percent NaS2O3 to remove excess iodine. The organic phase was isolated, dried (MgSO4), and evaporated. The residue was purified by column chromatography using 10percent EtOAc in heptane as eluent. The title compound (0.249 g, 53percent) was isolated as a white solid. NMR (DMSO-CZ6): δ 7.41 (s, 1 H), 6.64 (s, 1 H), 3.76 (s, 3H), 3.72 (s, 3H), 3.10 (m, 1H), 1.11 (d, 6H).
Reference: [1] Patent: WO2009/66060, 2009, A2. Location in patent: Page/Page column 100; 102
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