Hydrochloric Acid → 3-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid

HRID 1397379노트

반응식

HRID 1397379 반응식
Br[C:2]1[S:6][C:5]([C:7](=[O:12])[C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[C:13]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1)([OH:15])=[O:14].C([O-])([O-])=O.[Na+].[Na+].Cl>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:8]([F:11])([F:10])[C:7]([C:5]1[S:6][C:2]([C:20]2[CH:21]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:13]([OH:15])=[O:14])=[CH:3][CH:4]=1)=[O:12]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 27339573-Carboxyphenylboronic acidHCID 199715871-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethan-1-one

생성물 1

HCID 248966243-[5-(Trifluoroacetyl)thiophen-2-yl]benzoic Acid수율 79%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
90 °C

실험 절차

1-(5-Bromothiophen-2-yl)-2,2,2-trifluoroethanone (0.8 g, 3.09 mmol) and 3-carboxyphenylboronic acid (0.5 g, 3.01 mmol) were dissolved in DMF (10 mL) and the solution was purged with argon for 10 min. 2M aqueous solution of Na2CO3 (0.65 g, 6.17 mmol) and catalytic Pd(PPh3)4 (178 mg, 0.15 mmol) were added to the reaction mixture and heated to 90° C. for 10 h. The reaction mixture was cooled to room temperature, diluted with water and acidified to pH ˜6 with 1.5 N HCl. The crude product was extracted with EtOAc. The combined extracts were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was triturated with diethyl ether to get 3-(5-(2,2,2-trifluoroacetyl)thiophen-2-yl)benzoic acid (700 mg, yield 79%). 1H NMR (400 MHz, DMSO-d6) δ 13.35 (br s, 1H), 8.31-8.30 (m, 1H), 8.16-8.11 (m, 2H), 8.04-8.02 (d, J=7.6 Hz, 1H), 7.93-7.92 (d, J=4.3 Hz, 1H), 7.67-7.63 (t, J=7.8 Hz, 1H). MS (ESI) m/z: Calculated for C13H7F3O3S: 300.01. found: 299.0 (M−1)−.

후처리

  1. customthe solution was purged with argon for 10 min
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionThe crude product was extracted with EtOAc
  4. dry with materialThe combined extracts were dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-da787804e17c4d58a97be36234a06879
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901156B2

반응 노트

불러오는 중…