Potassium Carbonate → (7-Bromo-5-fluoro-2,3-dihydro-1-benzofuran-2-yl)methanol

HRID 2115999Notes

Reaction equation

HRID 2115999 reaction equation
[CH2:1]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([Br:11])[C:5]=1[OH:12])[CH:2]=[CH2:3].ClC1C=C(C=CC=1)C(OO)=[O:18].C(=O)([O-])[O-].[K+].[K+]>>[Br:11][C:6]1[C:5]2[O:12][CH:2]([CH2:3][OH:18])[CH2:1][C:4]=2[CH:9]=[C:8]([F:10])[CH:7]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 623681612-Allyl-6-bromo-4-fluorophenol

Product 1

HCID 68960862(7-Bromo-5-fluoro-2,3-dihydro-1-benzofuran-2-yl)methanolYield 78%

Procedure

Treatment of 2-allyl-6-bromo-4-fluorophenol (25.1 g, 0.109 mol) with 3-chloroperoxybenzoic acid (77%, 56.24 g, 0.326 mol) followed by potassium carbonate (62.19 g, 0.45 mol) generally according to the procedure described for Intermediate 9 provided 20.98 g (78%) of (±)-(7-bromo-5-fluoro-2,3-dihydro-1-benzofuran-2-yl)methanol as a white solid. Rf=0.54 (silica, ethyl acetate:hexanes 1:1); mp 53-57° C.; Anal. calcd. for C9H8BrFO2.0.1 C4H8O2: C, 44.13; H, 3.47. Found: C, 44.17; H, 3.16.

Sources & evidence

ORD record
ord-92b05b18616b4f9f9d4c62d646c81181
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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