Hydrochloric Acid → 4-(Benzyloxy)-3-bromobenzaldehyde

HRID 459160ノート

反応式

HRID 459160 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].[H-].[Na+].[CH2:13](Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl>CN(C)C=O>[CH2:13]([O:10][C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[Br:1])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 763083-Bromo-4-hydroxybenzaldehyde

生成物 1

HCID 14943384-(Benzyloxy)-3-bromobenzaldehyde収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-Bromo-4-hydroxy-benzaldehyde (1.9 g, 9.45 mmol) was added slowly, at 0° C., to a suspension of NaH 95% (290 mg, 11.34 nol) in dry N,N-dimethylformamide (45 mL). The mixture was stirred for 0.5 hours. Benzyl chloride (1.3 mL, 11.34 mmol) was added and the reaction stirred at room temperature overnight. 1N HCl (40 mL) was added and the layers separated. The aqueous layer was extracted with diethyl ether (5×50 mL) and the combined organic layers were dried (Na2SO4), filtered, and concentrated under vacuum. The residue was chromatographed (silica gel, hexanes/ethyl acetate 9:1) to produce 4-Benzyloxy-3-bromo-benzaldehyde as a white solid (2.47 g, 90%). 1H-NMR (CDCl3, 200.15 MHz): δ 9.82 (s, 1H), 8.09 (d, 1H, J=1.8), 7.76 (dd, 1H, J=8.4, 1.8), 7.47–7.32 (m, 5H), 7.02 (d, 1H, J=8.4), 5.24 (s, 2H.

後処理

  1. stirringthe reaction stirred at room temperature overnight
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with diethyl ether (5×50 mL)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was chromatographed (silica gel, hexanes/ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-9e89b2dd88924b45b55e0974239ed655
出典データセット
uspto-grants-2007_03
特許番号
US07192982B2

反応ノート

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