Dimethylformamide → HCID 20785532、化合物

HRID 1746065ノート

反応式

HRID 1746065 の反応式
[CH3:1]N(C)C=O.[Br:6][C:7]1[CH:8]=[C:9]([OH:15])[C:10]([OH:14])=[CH:11][C:12]=1[F:13].C(=O)([O-])[O-].[Cs+].[Cs+].BrCCl>CCOCC>[Br:6][C:7]1[C:12]([F:13])=[CH:11][C:10]2[O:14][CH2:1][O:15][C:9]=2[CH:8]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 6333BromochloromethaneHCID 10796Cesium carbonateHCID 218653784-Bromo-5-fluorobenzene-1,2-diol

生成物 1

HCID 20785532HCID 20785532、化合物収率 85%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To N,N-dimethylformamide (25 mL) in a 50 mL flask was added 4-bromo-5-fluorobenzene-1,2-diol (2 g, 9.66 mmol), cesium carbonate (4.72 g, 14.49 mmol) and bromochloromethane (1.875 g, 14.49 mmol). The reaction mixture was allowed to stir at room temperature for 1 h and was then heated to an external temperature of 80° C. for 3 h. Upon cooling, the reaction mixture was diluted with Et2O (75 mL) and washed with water (50 mL) followed by a wash with saturated NaCl solution (50 mL). The organic layer was dried over MgSO4 and filtered. Concentration of the organic solution gave 5-bromo-6-fluorobenzo[d][1,3]dioxole as a light orange solid (1.8 g, 85%): 1H NMR (400 MHz, CDCl3) δ 6.94 (d, J=5.9 Hz, 1H), 6.67 (d, J=7.9 Hz, 1H), 6.00 (s, 2H); 19F NMR (376 MHz, CDCl3) δ −113.82 (s); ESIMS m/z 220 ([M+H]+), 218 ([M−H]−).

後処理

  1. temperaturewas then heated to an external temperature of 80° C. for 3 h
  2. temperatureUpon cooling
  3. washwashed with water (50 mL)
  4. washa wash with saturated NaCl solution (50 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered

出典と根拠

ORDレコード
ord-22377facbfef4315be686cc7b49a830e
出典データセット
uspto-grants-2015_10
特許番号
US09149038B2

反応ノート

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