Potassium Carbonate → Methyl 3'-hydroxy-2'-methylbiphenyl-4-carboxylate

HRID 2307557Notes

Reaction equation

HRID 2307557 reaction equation
COC[O:4][C:5]1[C:6]([CH3:14])=[C:7](B(O)O)[CH:8]=[CH:9][CH:10]=1.I[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23]C)=[O:21])=[CH:18][CH:17]=1.C(=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[C:6]([CH3:14])=[C:7]([C:16]2[CH:26]=[CH:25][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 142891Ethyl 4-iodobenzoateHCID 226069353-Methoxymethoxy-2-methylbenzene-1-boronic acid

Product 1

HCID 22606879Methyl 3'-hydroxy-2'-methylbiphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolvent

Procedure

In a manner similar to that of Example 11(d), by reaction of 3.3 g (16.7 mmol) of 3-methoxymethoxy-2-methylbenzene-1-boronic acid (described in Example 11(c)) with 3 g (13.9 mmol) of ethyl 4-iodobenzoate, 16.7 mL of 2.0M potassium carbonate solution and 800 mg (0.69 mmol) of tetrakis(triphenylphosphine)palladium, followed by deprotection in methanol, the desired product is obtained in the form of a colourless oil (m=3.07 g; Y=77%).

Sources & evidence

ORD record
ord-ef0d4aa19c9a45fc9b8b61ba35be9808
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

Loading…