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Potassium Carbonate → Methyl 3'-hydroxy-3-methylbiphenyl-4-carboxylate

HRID 2307581
Notes
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Reaction equation

HRID 2307581 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.Br[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[C:17]([CH3:24])[CH:16]=1.[C:25](=O)([O-])[O-].[K+].[K+]>CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][C:5]1[CH:6]=[C:7]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([O:21][CH3:25])=[O:20])=[C:17]([CH3:24])[CH:16]=2)[CH:8]=[CH:9][CH:10]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 995704-Bromo-2-methylbenzoic acidHCID 22606941(3-(Methoxymethoxy)phenyl)boronic acid

Product 1

HCID 22606892Methyl 3'-hydroxy-3-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 887
Methanol
Solvent

Procedure

In a manner similar to that of Example 1(h), by reaction of 5.35 g (29 mmol) of 3-methoxymethoxyphenylboronic acid (described in Example 1(g)) and 5.7 g (26.7 mmol) of 4-bromo-2-methylbenzoic acid with 26.7 mL of 2.0M potassium carbonate and 1.54 g of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a colourless oil (m=3.22 g; Y=50%).

Sources & evidence

ORD record
ord-ebc3dcbdfc274e97ba2ab4a8ba0b6b55
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06831106B1

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes