Hydrochloric Acid → Methyl 3-acetyl-5-(methylsulfonyl)benzoic acid

HRID 1454197노트

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HRID 1454197 반응식
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([S:12]([CH3:15])(=[O:14])=[O:13])[CH:11]=1)[C:5]([O:7]C)=[O:6].[CH:16]([O:18]CCCC)=[CH2:17].[CH:23]1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:23][C:3]1[C:2]([C:16](=[O:18])[CH3:17])=[CH:11][C:10]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:9][C:4]=1[C:5]([OH:7])=[O:6]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 11430Potassium CarbonateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 22101072Methyl 3-bromo-5-methanesulfonylbenzoate

생성물 1

HCID 68830431Methyl 3-acetyl-5-(methylsulfonyl)benzoic acid수율 416.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
122 °C

실험 절차

A mixture of methyl 3-bromo-5-(methylsulfonyl)benzoate (66 mg, 0.226 mmol), 1-(vinyloxy)butane (45.3 mg, 0.06 mL, 0.452 mmol), palladium acetate (1.5 mg, 0.0068 mmol), DPPP (6.1 mg, 0.015 mmol) and potassium carbonate (37.5 mg, 0.27 mmol) in DMF (0.6 mL) and H2O (0.07 mL) in a Smith process vial was heated at 122° C. in microwave for 3 h. The reaction mixture was cooled down to room temperature and hydrolyzed by addition of 5% HCl (1 mL) slowly. The reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum. The crude mixture was purified by reverse phase prep HPLC to give the title compound (16 mg): 1H NMR (CD3OD, 500 MHz) δ ppm 2.74 (3H, s), 3.24 (3H, s), 8.70 (1H, m), 8.75 (1H, m), 8.87 (1H, m). HPLC retention time: 1.037 min (method A). MS (ESI) (M+H)+ 243.10.

후처리

  1. extractionThe reaction mixture was worked up by extraction with ethyl acetate and concentration under vacuum
  2. customThe crude mixture was purified by reverse phase prep HPLC

출처 및 근거

ORD 기록
ord-cf874909ecf14dec9f8a8c08fd3450dd
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476764B2

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