Chlorodifluoromethane → 1-Bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene

HRID 2171064ノート

反応式

HRID 2171064 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[C:3]=1[O:11][CH2:12][O:13][CH3:14].C(=O)([O-])[O-].[K+].[K+].Cl[CH:22]([F:24])[F:23]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:22]([F:24])[F:23])=[C:4]([O:9][CH3:10])[C:3]=1[O:11][CH2:12][O:13][CH3:14]

参加物

5

反応物 3

HCID 6372ChlorodifluoromethaneHCID 11430Potassium CarbonateHCID 674654874-Bromo-2-methoxy-3-(methoxymethoxy)phenol

生成物 1

HCID 674667461-Bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene収率 30%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
-45 °C

実験手順

To a stirring solution of 4-bromo-2-methoxy-3-(methoxymethoxy)phenol (700 mg, 2.66 mmol) in N,N-dimethylformamide (15 mL) was added potassium carbonate (734 mg, 5.32 mmol) cooled to −45° C. and chlorodifluoromethane (gas) was passed for 10 min and the resultant reaction mixture was heated to 80° C. for 2 h. The reaction mixture was quenched with ice-cold water and extracted with ethyl acetate (3×). The combined ethyl acetate layers were dried over anhy. sodium sulphate and concentrated under reduced pressure. Purification of the residue by flash column chromatography (silica gel, 0-5% ethyl acetate in pet ether) afforded 1-Bromo-4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)benzene as a liquid (250 mg, 30%).

後処理

  1. customthe resultant reaction mixture
  2. temperaturewas heated to 80° C. for 2 h
  3. customThe reaction mixture was quenched with ice-cold water
  4. extractionextracted with ethyl acetate (3×)
  5. dry with materialThe combined ethyl acetate layers were dried over anhy
  6. concentrationsodium sulphate and concentrated under reduced pressure
  7. customPurification of the residue by flash column chromatography (silica gel, 0-5% ethyl acetate in pet ether)

出典と根拠

ORDレコード
ord-43bec21ddde84183bc6f58eb1d6e98ce
出典データセット
uspto-grants-2015_06
特許番号
US09051290B2

反応ノート

読み込み中…