Sodium Carbonate → 2-Chloro-5-(3-methylphenyl)benzoic acid

HRID 404951Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:8](I)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1([CH3:21])[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([CH3:21])[CH:13]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

Conditions

Temperature: 50 °C

Procedure

2-Chloro-5-iodobenzoic acid (2.00 g, 7.08 mmol), m-tolylboronic acid (1.15 g, 8.50 mmol), Na2CO3 (2.70 g, 25.5 mmol) and Pd(OAc)2 (94 mg, 0.42 mmol) were dissolved in water (9 mL) and heated at 50° C. for 2 hours. The mixture was filtered and washed with water and filtrate was acidified with 2.5 M HCl, extracted into ethyl acetate and dried over anhydrous Na2SO4, the solvent was evaporated in vacuo to obtain crude 4-chloro-3′-methylbiphenyl-3-carboxylic acid as a grey solid in quantitative yield. 1H NMR (300 MHz, DMSO-d6): δ 8.03 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.63 (d, J=7.8 Hz, 1H), 7.55-7.50 (m, 2H), 7.40 (t, J=7.8 Hz, 1H), 7.25 (d, J=6.6 Hz, 1H), 2.41 (s, 3H).

Workup

filtrationThe mixture was filtered
washwashed with water and filtrate
extractionextracted into ethyl acetate
dry with materialdried over anhydrous Na2SO4
customthe solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-dd7a41a836704a808729cea1be660515
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748632B2

Reaction notes

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