2-Methylphenyl boronic acid → HCID 67215988, compound

HRID 1627953Notes

Reaction equation

HRID 1627953 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[CH2:11]OC2C=CC=CC=2)=[CH:5][CH:4]=1.[C:19]1([CH3:28])[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1B(O)O>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[CH2:11][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH3:28])=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 27332672-Methylphenyl boronic acidHCID 67215623HCID 67215623, compound

Product 1

HCID 67215988HCID 67215988, compoundYield 85.6%

Procedure

Following the general procedure using (E)-1-methoxy-4-(3-phenoxyprop-1-enyl)benzene (60 mg, 0.25 mmol), o-tolylboronic acid (51 mg, 0.38 mmol) and PdCl2(DPEphos) (0.015 mmol, 11 mg), the reaction was stirred for 6 h at rt. Column chromatography on silica gel (eluting with 3% EtOAc/hexanes) afforded the product as a colorless liquid (51 mg, 84%).

Sources & evidence

ORD record
ord-4d5151baabd7429aaf260968592e6949
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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