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Hydrochloric Acid → HCID 67527577, compound

HRID 2261762
Notes
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Reaction equation

HRID 2261762 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[CH3:10][O:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.CN(C=O)C.Cl>O.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>[CH3:10][O:11][C:12](=[O:24])[CH:13]=[CH:14][C:15]1[CH:16]=[CH:17][C:18]([C:2]2[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=2[CH3:9])=[CH:19][CH:20]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 728574-Bromo-m-cresolHCID 5708389[4-(E-3-Methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid

Product 1

HCID 67527577HCID 67527577, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-3-methyl-phenol (460 mg, 2.01 mmol), [4-(E-3-methoxy-3-oxo-1-propen-1-yl)phenyl]boronic acid (486 mg, 2.21 mmol), tetrakis(triphenylphosphine)palladium(0) (232 mg, 0.201 mmol) cesium carbonate (1.31 g, 4.02 mmol) and DMF (4.8 mL) is heated to 80° C. for 4.5 hours. The reaction is cooled to room temperature and diluted with water and acidified with 1 N HCl. The resulting solution is extracted with ether. The combined organic layers are dried over anhydrous magnesium sulfate and are purified via flash chromatography eluting with 15% ethyl acetate/heptane to give the title compound (108 mg, 20%). ES/MS m/e 267.3 (M−1).

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionThe resulting solution is extracted with ether
  3. dry with materialThe combined organic layers are dried over anhydrous magnesium sulfate
  4. customare purified via flash chromatography
  5. washeluting with 15% ethyl acetate/heptane

Sources & evidence

ORD record
ord-e5e5de10b6244727a3ac18289e21fd63
Source dataset
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07846960B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes