Sulfuryl chloride → 2-Chloro-4-(2,2,2-trifluoroethoxy)phenol

HRID 51078ノート

反応式

HRID 51078 の反応式
[F:1][C:2]([F:13])([F:12])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.S(Cl)([Cl:17])(=O)=O>C(NCC(C)C)C(C)C.C1(C)C=CC=CC=1>[Cl:17][C:7]1[CH:6]=[C:5]([O:4][CH2:3][C:2]([F:12])([F:13])[F:1])[CH:10]=[CH:9][C:8]=1[OH:11]

参加物

5

反応物 2

HCID 24648Sulfuryl chlorideHCID 130853484-(2,2,2-Trifluoroethoxy)phenol

生成物 1

HCID 227373642-Chloro-4-(2,2,2-trifluoroethoxy)phenol収率 106.1%

試薬・触媒・溶媒 2

HCID 8085Diisobutylamine触媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

To a 30 ml toluene solution of 4-(2,2,2-trifluoroethoxy)phenol (1.02 g, 5.31 mmol) and diisobutylamine (0.074 ml, 0.42 mmol) was added sulfuryl chloride (0.38 ml, 4.7 mmol). This solution was heated to 70° C. for 2 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and sat. bicarb. solution. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel eluting with 10% AcOEt/hexanes to give the title compound as a pale yellow oil 1.13 g (94%).

後処理

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and sat. bicarb
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel eluting with 10% AcOEt/hexanes

出典と根拠

ORDレコード
ord-155ed8dcc6f14da493eeb5ee528efb71
出典データセット
uspto-grants-2004_03
特許番号
US06713508B2

反応ノート

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