(4-Methoxyphenyl)boronic acid → HCID 10471704, compound

HRID 2308257Notes

Reaction equation

HRID 2308257 reaction equation
Br[C:2]1[C:6]([CH3:7])=[C:5](I)[S:4][C:3]=1[CH:9]1[O:13]CCO1.[F:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][C:20]=1[O:21]C.C[O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1>>[F:14][C:15]1[CH:16]=[C:17]([C:5]2[S:4][C:3]([CH:9]=[O:13])=[C:2]([C:31]3[CH:32]=[CH:33][C:28]([OH:27])=[CH:29][CH:30]=3)[C:6]=2[CH3:7])[CH:18]=[CH:19][C:20]=1[OH:21]

Participants

4

Reactant 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 27821943-Fluoro-4-methoxyphenylboronic acidHCID 22601716HCID 22601716, compound

Product 1

HCID 10471704HCID 10471704, compoundYield 86%

Procedure

Starting from 2-(3-bromo-5-iodo-4-methylthien-2-yl)-1,3-dioxolane (2.3 g, 6.1 mmol) and 3-fluoro-4-methoxyphenylboronic acid (1.6 g, 9.4 mmol) in place of 4-methoxyphenylboronic acid (Step 1), and substituting 4-methoxyphenylboronic acid in place of 3-methoxyphenylboronic acid (Step 2), the title compound (0.42 g, 86%, m.p. 227-29° C.) was synthesized in essentially the same manner as described in Example 1.

Sources & evidence

ORD record
ord-a29c60be3a9e4415985f20ab3f21924e
Source dataset
uspto-grants-2004_12
Patent number
US06835745B2

Reaction notes

Loading…