Potassium Carbonate → 1-[4-(3-Hydroxyphenyl)-2-thiophenyl]-1-propanone

HRID 2307573

Reaction equation

HRID 2307573 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.Br[C:15]1[CH:16]=[C:17]([C:20](=[O:23])[CH2:21][CH3:22])[S:18][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:16]=[C:17]([C:20](=[O:23])[CH2:21][CH3:22])[S:18][CH:19]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 8189324-Bromo-2-propionylthiopheneHCID 22606941(3-(Methoxymethoxy)phenyl)boronic acid

Product 1

HCID 226069201-[4-(3-Hydroxyphenyl)-2-thiophenyl]-1-propanone

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

In a manner similar to that of Example 1(h), by reaction of 4.6 g (25 mmol) 3-methoxymethoxyphenylboronic acid (described in Example 1(g)) and 5 g (22.8 mmol) of 1-(4-bromo-2-thiophenyl)-1-propanone with 22.8 mL of 2.0M potassium carbonate and 1.32 g of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a white solid (m.p.=112° C.; m=3.87 g: Y=73%).

Sources & evidence

ORD record
ord-a3dfd4a2b2664d89af009c56b11c1896
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Linked notes

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