3-Bromo-5-fluorophenol → 3-(Benzo[d]thiazol-5-yl)-5-fluorophenol

HRID 1965844Notes

Reaction equation

HRID 1965844 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=1.CC1(C)C(C)(C)OB([C:18]2[CH:19]=[CH:20][C:21]3[S:25][CH:24]=[N:23][C:22]=3[CH:26]=2)O1>>[S:25]1[C:21]2[CH:20]=[CH:19][C:18]([C:2]3[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([F:8])[CH:7]=3)=[CH:26][C:22]=2[N:23]=[CH:24]1

Participants

3

Reactant 2

HCID 219046363-Bromo-5-fluorophenolHCID 467390305-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole

Product 1

HCID 592829253-(Benzo[d]thiazol-5-yl)-5-fluorophenol

Procedure

Compound 3-(benzo[d]thiazol-5-yl)-5-fluorophenol (W190) was prepared using the general procedure for Suzuki coupling reaction between 3-bromo-5-fluorophenol (57 mg, 0.3 mmol) and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazole (78 mg, 0.3 mmol), as a white solid (60 mg, 81%). 1H NMR (400 MHz, acetone-d6) δ 9.30 (s, 1 H), 9.02 (brs, 1 H), 8.30 (d, J=1.6 Hz, 1 H), 8.19 (d, J=8.4 Hz, 1 H), 7.45 (dd, J=8.4, 2.0 Hz, 1 H), 7.07 (t, J=1.6 Hz, 1 H), 7.02 (dt, J=10.0, 2.0 Hz, 1 H), 6.64 (dt, J=10.4, 2.4 Hz, 1 H); MS (ESI) m/z 275 (M+H+).

Sources & evidence

ORD record
ord-7d639a515686441b9d26f1d08df24189
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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