Benzyl Bromide → 4-(Benzyloxy)-2,6-dichlorobenzaldehyde

HRID 1161764ノート

反応式

HRID 1161764 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[Cl:1][C:2]1[CH:9]=[C:8]([O:10][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5283822,6-Dichloro-4-hydroxybenzaldehyde

生成物 1

HCID 111502104-(Benzyloxy)-2,6-dichlorobenzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Treat a mixture of 2,6-dichloro-4-hydroxy-benzaldehyde (250 g, 1.3 mol) and potassium carbonate (361.8 g, 2.62 mol) in 2 L dimethylformamide with benzyl bromide (268.64 g, 1.57 mol). Stir the reaction at room temperature for 1 hour. Filter off solids and pour into 12 L of water. Filter off solid, wash several times with water, air dry and dissolve in ethyl acetate. Dry over magnesium sulfate, filter and concentrate under vacuum to ˜1.5 L. Allow to sit overnight then filter. Wash solid with minimal amount of hexane and vacuum dry. Concentrate the filtrate under vacuum and triturate with hexane to yield a second crop of product which when combined with the first crop equals 245 g white crystals. Repeat to obtain a 3rd crop of 80 g as a light-tan powder (88% overall yield): 1H NMR (400 MHz, DMSO-d6) δ 10.26 (s, 1H), 7.43 (m, 5H), 7.28 (s, 2H), 5.25 (s, 2H).

後処理

  1. additionTreat
  2. customthe reaction at room temperature for 1 hour
  3. filtrationFilter off solids
  4. additionpour into 12 L of water
  5. filtrationFilter off solid
  6. washwash several times with water, air
  7. customdry
  8. dissolutiondissolve in ethyl acetate
  9. dry with materialDry over magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate under vacuum to ˜1.5 L
  12. filtrationthen filter
  13. washWash solid with minimal amount of hexane and vacuum
  14. customdry
  15. concentrationConcentrate the filtrate under vacuum
  16. customtriturate with hexane
  17. customto yield a second crop of product which when
  18. customRepeat to obtain a 3rd crop of 80 g
  19. customas a light-tan powder (88% overall yield)

出典と根拠

ORDレコード
ord-739837224d77445ea27e53b00e05b325
出典データセット
uspto-grants-2010_10
特許番号
US07820659B2

反応ノート

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