4-Chlorophenylboronic acid → 1-Chloro-4-cinnamylbenzene

HRID 1627954Notes

Reaction equation

HRID 1627954 reaction equation
[CH2:1](OC1C=CC=CC=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:1][CH:2]=[CH:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 258010Cinnamyloxybenzene

Product 1

HCID 2447691-Chloro-4-cinnamylbenzeneYield 75.2%

Procedure

Following the general procedure using cinnamyloxybenzene (53 mg, 0.25 mmol), 4-chlorophenylboronic acid (58 mg, 0.38 mmol) and PdCl2(D-t-BPF) (0.015 mmol, 9.8 mg), the reaction was stirred for 20 h at rt. Column chromatography on silica gel (eluting with 3% EtOAc/hexanes) afforded the product as a colorless liquid (43 mg, 75%).

Sources & evidence

ORD record
ord-6e4b5313a6ce4f2e9bb873be69354914
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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