3-Chlorobenzoic Acid → 2'-Methyl-biphenyl-3-carboxylic acid

HRID 227903

반응식

HRID 227903 반응식
Cl[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]1([CH3:20])[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O.[Pd].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+]>[CH3:20][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([OH:7])=[O:6])[CH:3]=1

참가 물질

8

반응물 3

HCID 4473-Chlorobenzoic AcidHCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acid

생성물 1

HCID 27598142'-Methyl-biphenyl-3-carboxylic acid수율 96%

시약·촉매·용매 4

HCID 23938Palladium촉매2회HCID 167845palladium(II) acetate촉매HCID 23677046Sodium 2'-(dicyclohexylphosphino)-2,6-dimethoxybiphenyl-3-sulfonate촉매HCID 962Water용매2회

실험 절차

Using 0.1 mol % Pd. The general procedure described in Example 3 was used with 3-chlorobenzoic acid (157 mg, 1.00 mmol), o-tolylboronic acid (163 mg, 1.20 mmol), K2CO3 (345 mg, 2.50 mmol), water (1.5 mL), Pd/L solution (0.200 mL of a Pd(OAc)2 (1.1 mg, 0.005 mmol, 0.5 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (5.0 mg, 0.010 mmol, 1 mol %) solution in 1.0 mL water), 6 h, 100° C. The product was isolated as a white solid (203 mg, 96%). Mp=127° C. 1H NMR (400 MHz, CDCl3) δ: 12.9 (br-s, 1H), 8.01 (m, 2H), 7.46 (d, 1H, J=7.6 Hz), 7.40 (t, 1H, J=7.6 Hz), 7.20-7.14 (m, 4H), 2.17 (s, 3H). 13C NMR (125 MHz, CDCl3) δ: 172.8, 142.5, 140.8, 135.5, 134.8, 131.1, 130.7, 129.9, 129.4, 128.8, 128.5, 127.9, 125.2, 20.6. IR (neat, cm−1): 2962, 1689, 1309, 1258, 747. Anal. Calcd for C14H12O2: C, 79.22; H, 5.70. Found: C, 79.12; H, 5.62.

출처 및 근거

ORD 기록
ord-3031c8344c054c418869742a399698a4
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560596B2

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