Sodium Carbonate → HCID 21931579, compound

HRID 1183114Notes

Reaction equation

HRID 1183114 reaction equation
Br[C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=1.[OH:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O1CCOCC1>[OH:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[S:6][C:5]([C:7](=[O:9])[CH3:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 793352-Acetyl-5-bromothiopheneHCID 27343604-Hydroxyphenylboronic acid

Product 1

HCID 21931579HCID 21931579, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A flame-dried test tube under N2 was charged with 1-(5-bromothiophen-2-yl)ethanone (250 mg, 1.22 mmol), p-hydroxyphenylboronic acid (1.2 equiv, 1.40 mmol, 202 mg), and 2.0 mL 1,4-dioxane. To the yellow solution, tetrakistriphenylphosphinepalladium(0) (6 mol %, 0.0731 mmol, 84 mg) and 2 M aqueous sodium carbonate (2.0 equiv, 2.44 mmol, 2.0 mL) were added. The yellow mixture was heated to 100° C. for 18 h. The resulting yellow-brown mixture was cooled to rt, adsorbed onto Celite in vacuo, and purified by silica gel chromatography to afford the desired product as an analytically pure yellow solid (51 mg, 19% yield).

Workup

  1. temperatureThe resulting yellow-brown mixture was cooled to rt
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b7c792fb287b43b4bdf635222b91525b
Source dataset
uspto-grants-2014_03
Patent number
US08664255B2

Reaction notes

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