Potassium Phosphate, Tribasic → HCID 68686708, compound

HRID 2244231Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1Br.[C:13]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)([OH:15])=[O:14].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1OCCOC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:19]1[CH:20]=[CH:21][C:16]([C:13]([OH:15])=[O:14])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl (2-bromophenyl)acetate of Step A (20.0 g, 87.3 mmol), 4-carboxybenzeneboronic acid (14.5 g, 87.4 mmol), [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium [II] (3.6 g, 4.4 mmol) and potassium phosphate (55.6 g, 262 mmol) in dry 4-dioxane (ca. 400 mL) was heated at 100° C. with vigorous stirring for 17 hours. The cooled mixture was then filtered through Celite and washed with 1,4-dioxane (ca. 200 mL). The filtrate was concentrated in vacuo to give a tacky brown solid (28.0 g). Purification by flash chromatography using a solvent gradient of 320:1:1 to 80:1:1 dichloromethane/acetic acid/methanol afforded an impure tacky orange solid (11.9 g). The solid product was dissolved in ethyl acetate (300 mL), filtered from insoluble material, and the filtrate washed with water (2×150 mL) and brine (150 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo to give a light orange solid (7.3 g). Recrystallization from diethyl ether provided the title compound (5.2 g, 22%) as pale orange needles.

Workup

filtrationThe cooled mixture was then filtered through Celite
washwashed with 1,4-dioxane (ca. 200 mL)
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-186b0a4ff04e43088893e37628bafc38
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678787B2

Reaction notes

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