Hydrochloric Acid → 5-Bromo-[1,1'-biphenyl]-2-carboxylic acid

HRID 1499122Notes

Reaction equation

Br[C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN1C(=O)CCC1.O>[Br:11][C:9]1[CH:10]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2,4-dibromo-benzoic acid, (2.3 g, 18.8 mmol), phenyl boronic acid (5 g, 17.9 mmol), Pd2(dba)3 (818 mg, 8.9 mmol) and LiOH (1.65 g, 39.3 mmol) in a 1:1 mixture of NMP/water (100 mL) was heated to 70° C. for 2 d. After this time, the reaction mixture was cooled to RT, and the reaction mixture was adjusted to pH=4-5 with 3 N HCl. The mixture was then extracted with ethyl acetate and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and purified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1) to afford 5-bromo-[1,1′-biphenyl]-2-carboxylic acid as a colorless oil.

Workup

temperatureAfter this time, the reaction mixture was cooled to RT
extractionThe mixture was then extracted with ethyl acetate
washthe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1)

Sources & evidence

ORD record: ord-20381d8e3b20480f9535fbeed6a5cd8c
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199994B2

Reaction notes

Loading…