Potassium Carbonate → Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate

HRID 68598

반응식

HRID 68598 반응식
[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6](Br)[CH:5]=1)(=[O:3])[CH3:2].[F:17][C:18]([F:29])([F:28])[C:19]1[CH:20]=[C:21](B(O)O)[CH:22]=[CH:23][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(C)C.O.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([C:4]1[CH:15]=[CH:14][C:7]([O:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[C:6]([C:23]2[CH:22]=[CH:21][CH:20]=[C:19]([C:18]([F:29])([F:28])[F:17])[CH:24]=2)[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 66868355Methyl 2-(4-acetyl-2-bromophenoxy)acetate

생성물 1

HCID 66868647Methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate수율 74%

시약·촉매·용매 4

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

Methyl 2-(4-acetyl-2-bromophenoxy)acetate (16) (710 mg, 2.5 mmol, 1 eq), 3-(trifluoromethyl)phenylboronic acid (709 mg, 3.75 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) and tetrakis(triphenylphosphine) palladium (100 mg, 0.086 mmol, 0.03 eq) were dissolved in t-BuOH (1 mL) and K2CO3 (1 mL of a 4 M solution in H2O) and heated in a microwave at 120° C. for 20 min. The resultant reaction mixture was diluted with EtOAc, washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The obtained residue was purified via silica gel chromatography (20% EtOAc/hexane) to give 650 mg (74%) of methyl 2-(4-acetyl-2-(3-trifluoromethylphenyl)phenoxy)acetate (17) as white solid. 1HNMR (CDCl3, 400 MHz): δ 8.43 (s, 2H), 7.90 (m, 2H), 7.60 (m, 2H), 6.89 (d, 1H), 4.72 (s, 2H), 3.79 (s, 3H), 2.59 (s, 3H). MS (ES-API): M+1=353.1. HPLC (Method B) tR=3.28 min.

후처리

  1. customThe resultant reaction mixture
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified via silica gel chromatography (20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-16b8d4de58c946429df3be172cccdbe0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822467B2

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