Potassium Carbonate → (7-Bromo-2,3-dihydrobenzofuran-2-yl)methanol

Reaction equation

[CH2:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[OH:11])[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:17].C(=O)([O-])[O-].[K+].[K+]>>[Br:10][C:6]1[C:5]2[O:11][CH:2]([CH2:3][OH:17])[CH2:1][C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

Reactant 3

HCID 11430Potassium Carbonate

HCID 70297m-Chloroperbenzoic acid

HCID 132186452-Bromo-6-(prop-2-en-1-yl)phenol

Product 1

HCID 59858092(7-Bromo-2,3-dihydrobenzofuran-2-yl)methanolYield 74.3%

Procedure

Treatment of 2-allyl-6-bromophenol (61.4 g 0.288 mol) with 3-chloroperoxybenzoic acid (77%, 149.18 g, 0.864 mol)) followed by potassium carbonate (99.56 g, 0.72 mol) generally according to the procedure described for Intermediate 9 provided 49.00 g (78%) (86%) of (±)-(7-bromo-2,3-dihydro-1-benzofuran-2-yl)methanol as an amber oil. Rf=0.66 (silica, ethyl acetate:hexanes 1:9) 1H NMR (DMSO-d6) δH 7.23 (dd, 1H); 7.14 (dd, 1H); 6.71 (t, 1H); (5.01 m, 1H); 4.85 (m, 1H); 4.99 (m, 2H); 3.36 (d, 2H).