Trifluoroacetic acid → [5-Formyl-6-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-acetic acid methyl ester

HRID 983808Notes

Reaction equation

HRID 983808 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:10]=[C:9]([CH:11]=[O:12])[C:8]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:7](Br)[CH:6]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC#N.O.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].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>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1[CH:6]=[C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:8]([O:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])=[C:9]([CH:11]=[O:12])[CH:10]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 66827Phenylboronic AcidHCID 18373917Acetonitrile--water (1/1)HCID 54469909Methyl 2-(3-bromo-5-formyl-4-((2-methoxyethoxy)methoxy)phenyl)acetate

Product 1

HCID 54196773[5-Formyl-6-(2-methoxy-ethoxymethoxy)-biphenyl-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 11430Potassium CarbonateSolvent

Conditions

Temperature
70 °C

Procedure

The arylbromide (5) (118 mmol, 42.6 gr) was dissolved in about 430 ml of toluene in a 1 L flask to which 150 ml of 2M K2CO3 was added followed by 5.0 g (0.037 eq) of Pd(PPh3)4. After the addition of phenylboronic acid (2.0 eq, 29 gr) the flask was heated to 70° C. and the mixture stirred for 5 hours. HPLC of the reaction mixture indicated that the arylbromide had completely reacted and a dominant less polar moiety (89% pure, r.t.=8.5 min., 1-90% MeCN/H2O, 0.1% TFA) was observed.

Workup

  1. additionwas added
  2. customhad completely reacted

Sources & evidence

ORD record
ord-38d3785efda347b398acf25214fa01ae
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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