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

HRID 68598

反応式

HRID 68598 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-16b8d4de58c946429df3be172cccdbe0
出典データセット
uspto-grants-2014_09
特許番号
US08822467B2

関連ノート

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