4-Bromo-2-fluorophenol → 4-(Benzo[d]thiazol-5-yl)-2-fluorophenol

HRID 1965841Notes

Reaction equation

HRID 1965841 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=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:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=3)=[CH:26][C:22]=2[N:23]=[CH:24]1

Participants

3

Reactant 2

HCID 27249814-Bromo-2-fluorophenolHCID 467390305-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzothiazole

Product 1

HCID 592830924-(Benzo[d]thiazol-5-yl)-2-fluorophenol

Procedure

Compound 4-(benzo[d]thiazol-5-yl)-2-fluorophenol (W121) was prepared using the general procedure for Suzuki coupling reaction between 4-bromo-2-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 (45 mg, 61%). 1H NMR (400 MHz, acetone-d6) δ 9.27 (s, 1 H), 8.85 (s, 1 H), 8.28 (d, J=1.6 Hz, 1 H), 8.15 (d, J=8.4 Hz, 1 H), 7.75 (dd, J=8.4, 1.6 Hz 1 H), 7.55 (dd, J=12.4, 2.4 Hz, 1 H), 7.45 (m, 1 H), 7.12 (t, 9.2 Hz, 1 H); MS (ESI) m/z 246 (M+H+).

Sources & evidence

ORD record
ord-04c079be80e24191a876e582231e42f3
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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