Potassium Carbonate → HCID 71245628, compound

HRID 1038310Notes

Reaction equation

HRID 1038310 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].Br[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([B:19]2[O:27][C:24]([CH3:26])([CH3:25])[C:21]([CH3:23])([CH3:22])[O:20]2)=[CH:15][CH:14]=1.C(=O)([O-])[O-:29].[K+].[K+]>CN(C=O)C>[CH3:22][C:21]1([CH3:23])[C:24]([CH3:26])([CH3:25])[O:27][B:19]([C:16]2[CH:17]=[CH:18][C:13]([CH2:12][O:29][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[C:3](=[O:4])[CH3:2])=[CH:14][CH:15]=2)[O:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68490alpha-HydroxyacetophenoneHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane2×

Product 1

HCID 71245628HCID 71245628, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-hydroxy-acetophenone (0.3 g, 2.2 mmol), 4-bromomethylphenylboronic acid pinacol ester (0.8 g, 2.7 mmol) and potassium carbonate (0.3 g, 2.2 mmol) in DMF (5 ml) was heated up to 110° C. for 24 h. The reaction mixture composition was determined by TLC and 4-bromomethylphenylboronic acid pinacol ester (0.3 g, 1.0 mmol) was added. The reaction mixture was heated to 110° C. for additional 24 h. The solvent was removed in vacuo. The crude product was purified by column chromatography on silica (CH2Cl2 to 4% MeOH) to give the desired product as an oil (0.51 g, 1.4 mmol, 64%). δH (CDCl3, 400 MHz): 1.24 (12H, s, CH3), 2.59 (3H, s, COCH3), 6.98 (1H, dd, 3J=9.2, 4J=1.6), 7.00 (1H, dd, 3J=8.4, 4J=0.8), 7.41 (1H, dd, 4J=4), 7.43 (2H, d, 3J=8.4), 7.74 (1H, dd, 3J=7.6, 4J=1.6), 7.83 (2H, d). δC (CDCl3, 125 MHz): 24.91 (CH3), 32.15 (COCH3), 70.62 (Cqart), 83.95 (CH2), 112.80 (CAr), 120.93 (CAr), 126.78 (CAr), 128.72 (CAr), 130.52 (CAr), 133.62 (CAr), 135.16 (CAr), 139.23 (CAr), 158.00 (CAr), 199.93 (CO). m/z (ES+) 391.1 [M+K]+ calc for C21H25BKO4391.2.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was heated to 110° C. for additional 24 h
  3. customThe solvent was removed in vacuo
  4. customThe crude product was purified by column chromatography on silica (CH2Cl2 to 4% MeOH)

Sources & evidence

ORD record
ord-340649cac4ef4284afa06ef7eb27428a
Source dataset
uspto-grants-2013_10
Patent number
US08551976B2

Reaction notes

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