Methanol → 1,4-Dibromo-2-methoxybenzene

HRID 2384928ノート

反応式

HRID 2384928 の反応式
C[C:2](C)([O-:4])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1F.CO>C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][C:9]=1[O:4][CH3:2]

参加物

5

反応物 3

HCID 887MethanolHCID 1370041,4-Dibromo-2-fluorobenzeneHCID 23665647Potassium tert-butoxide

生成物 1

HCID 133995571,4-Dibromo-2-methoxybenzene収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

Add dropwise potassium tert-butoxide (118.2 ml, 118.2 mmol, 1 M in hexane) to a solution of 1,4-dibromo-2-fluorobenzene (25.0 g, 98.5 mmol) in THF (492 mL) and MeOH (40 mL, 984.7 mmol) at RT. Heat the mixture at 70° C. overnight. Quench the mixture with water (50 mL), dilute with Et2O (400 mL), wash once with saturated NH4Cl (300 mL) and back extract the aqueous with Et2O (200 mL). Dry the combined organic phase over Na2SO4, filter, and concentrate. Purify the crude material by flash chromatograph, eluting with 5-10% ethylacetate/hexane to give 22.0 g (84%) of the title compound. GC m/z (79Br81Br) 266 [M]+.

後処理

  1. customQuench the mixture with water (50 mL)
  2. additiondilute with Et2O (400 mL)
  3. washwash once with saturated NH4Cl (300 mL)
  4. extractionback extract the aqueous with Et2O (200 mL)
  5. dry with materialDry the combined organic phase over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify the crude material by flash chromatograph
  9. washeluting with 5-10% ethylacetate/hexane

出典と根拠

ORDレコード
ord-4859eb24b11242a09b20888a638cf701
出典データセット
uspto-grants-2012_09
特許番号
US08263772B2

反応ノート

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