Benzyl Bromide → 4-(3-Benzyloxycarbonyl-propyl)-phenylboronic acid
Reaction equation
[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13]OC1C=CC(B(O)O)=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[B:24]([C:27]1[CH:32]=[CH:31][C:30](CCCC(O)=O)=[CH:29][CH:28]=1)([OH:26])[OH:25].C(Br)C1C=CC=CC=1>>[CH2:1]([O:8][C:9]([CH2:11][CH2:12][CH2:13][C:30]1[CH:31]=[CH:32][C:27]([B:24]([OH:26])[OH:25])=[CH:28][CH:29]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Procedure
Using a procedure analogous to that used to prepare 1B, 2B (212 mg, 1:1 mixture of 2B and 2A) was reacted with benzyl bromide to afford 2C (90 mg, 69%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.92 (m, 2H), 2.33 (t, J=7.0 Hz, 2H), 2.62 (t, 2H), 5.08 (s, 2H), 7.11 (d, 2H), 7.25-7.35 (m, 5H), 7.69 (d, 2H).