Dimethylformamide → Tert-butyl 4'-(3-hydroxypropyl)biphenyl-2-carboxylate

HRID 1927642Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][OH:18])=[CH:11][CH:10]=2)O1.I[C:21]1[CH:33]=[CH:32][CH:31]=[CH:30][C:22]=1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O>[OH:18][CH2:17][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([C:21]2[C:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[CH:30][CH:31]=[CH:32][CH:33]=2)=[CH:10][CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanol (37.9 mmol), tert-butyl 2-iodobenzoate (11.5 g, 37.9 mmol), sodium carbonate (10 g, 94.8 mmol), 1,1′-bis(diphenylphosphino)ferroncene-palladium dichloride dichloromethane complex (1:1), DMF (170 mL) and water (22 mL) was heated at 80° C. under nitrogen overnight. The reaction mixture was cooled to RT, poured into water, and the product was extracted with EtOAc-Hexanes (1:1). The combined organic extracts were washed with water and brine, dried (Na2SO4) and concentrated, and the residue was purified on silica gel (Hexane/EtOAc, from 2/1 to 1/1) to afford tert-butyl 4′-(3-hydroxypropyl)biphenyl-2-carboxylate.

Workup

temperatureThe reaction mixture was cooled to RT
extractionthe product was extracted with EtOAc-Hexanes (1:1)
washThe combined organic extracts were washed with water and brine
dry with materialdried (Na2SO4)
concentrationconcentrated
customthe residue was purified on silica gel (Hexane/EtOAc, from 2/1 to 1/1)

Sources & evidence

ORD record: ord-da736bc2073a415c8bc693dd9ebda083
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183275B2

Reaction notes

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