3-Chlorobenzoic Acid → HCID 86606934, compound

HRID 227911Notes

Reaction equation

HRID 227911 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O)=[O:12].C([O-])([O-])=O.[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].O>[OH2:6].[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1)=[O:12]

Participants

7

Reactant 3

HCID 4473-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acid

Product 1

HCID 86606934HCID 86606934, compoundYield 157.2%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonateCatalystHCID 962WaterSolvent

Procedure

The general procedure described in Example 3 was used with 3-chlorobenzoic acid (157 mg, 1.00 mmol), 2-formylphenylboronic acid (225 mg, 1.50 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (414 mg, 3.00 mmol), water (2.0 mL), 10 h, 80° C. The product was isolated as a white solid (192 mg, 85%). Mp=164-167° C. 1H NMR (400 MHz, d4-MeOH, d6-DMSO) δ: 8.07 (m, 2H), 7.68 (m, 1H), 7.63-7.52 (m, 2H), 7.46 (m, 2H), 7.30 (m, 1H), 5.10 (s, 1H), 4.98 (br-s, 2H). 13C NMR (125 MHz, d4-MeOH, d6-DMSO) δ: 169.4, 142.1. 142.0, 137.0, 135.0, 131.9, 131.7, 131.2, 129.9, 129.8, 129.6, 128.9, 127.8, 103.6 [Ar—CH(OH)2] IR (neat, cm−1): 3066, 1694, 1260, 754.

Sources & evidence

ORD record
ord-5ce208a93ae9444ca5ec43ce45a7544c
Source dataset
uspto-grants-2009_07
Patent number
US07560596B2

Reaction notes

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