1,4-Dibromobenzene → 1-(4-Bromophenyl)cyclobutanol

HRID 9233

反応式

HRID 9233 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[C:14]1(=[O:18])[CH2:17][CH2:16][CH2:15]1>C1COCC1>[Br:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]2([OH:18])[CH2:17][CH2:16][CH2:15]2)=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 78041,4-DibromobenzeneHCID 14496CyclobutanoneHCID 178418339Butyllithium

生成物 1

HCID 120954191-(4-Bromophenyl)cyclobutanol収率 54%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

n-Butyllithium (1.2 mL 1.92 mmol, 1.6 M/hexanes) was added to a −78° C. solution of 1,4-dibromobenzene (489 mg, 2.07 mmol) in THF (4.2 mL). After 30 min., a solution of cyclobutanone (141 mg, 2.01 mmol) in 1 mL THF was added by cannula, rinsing with 0.5 mL THF. The reaction was allowed to warm to room temperature and after 2 h, saturated NH4Cl solution was added. The resulting mixture was extracted with ethyl acetate (3×30 mL) and the combined ethyl acetate solution was washed with brine. The solution was then dried (Na2SO4), filtered and evaporated. Purification by flash chromatography on silica gel (5%→10% ethyl acetate/hexanes) gave 3-1 (235 mg, 54%).

後処理

  1. washrinsing with 0.5 mL THF
  2. additionsaturated NH4Cl solution was added
  3. extractionThe resulting mixture was extracted with ethyl acetate (3×30 mL)
  4. washthe combined ethyl acetate solution was washed with brine
  5. dry with materialThe solution was then dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography on silica gel (5%→10% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-a1ca73b0fd194eeaa31cf248b261c57b
出典データセット
uspto-grants-2006_08
特許番号
US07091231B2

関連ノート

読み込み中…