(3,5-Di-tert-butyl-2-propoxyphenyl)boronic acid → 3-(3',5'-di-tert-butyl-6-hydroxy-2'-propyloxy-3-biphenylyl)acrylic Acid

HRID 988053Notes

Reaction equation

HRID 988053 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]([O:13]CC)=[O:12])[CH:5]=[CH:6][C:7]=1[OH:8].[CH2:16]([O:19][C:20]1[C:25]([C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:24][C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:22][C:21]=1B(O)O)[CH2:17][CH3:18]>>[C:26]([C:25]1[C:20]([O:19][CH2:16][CH2:17][CH3:18])=[C:21]([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])[CH:3]=2)[CH:22]=[C:23]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

3

Reactant 2

HCID 22345485(3,5-Di-tert-butyl-2-propoxyphenyl)boronic acidHCID 69793988Ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate

Product 1

HCID 697927313-(3',5'-di-tert-butyl-6-hydroxy-2'-propyloxy-3-biphenylyl)acrylic AcidYield 4.6%

Procedure

In a manner similar to that of Example 1(c), by reaction of 1.0 g (3.7 mmol) of ethyl 3-(3-bromo-4-hydroxyphenyl)acrylate obtained in Example 34(d) with 2.14 g (7.33 mmol) of 2-propyloxy-3,5-di-tert-butylphenylboronic acid obtained above, 70 mg (4%) of the expected compound were obtained in the form of a colorless oil.

Sources & evidence

ORD record
ord-0b5e2ec8b0b44619ab43c8a326945a67
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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