5-(Benzyloxy)-2-bromobenzaldehyde → 4-(Benzyloxy)-1-bromo-2-vinylbenzene

HRID 860706ノート

反応式

HRID 860706 の反応式
[CH3:1]C(C)([O-])C.[K+].[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:22]=1)[CH:20]=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1OCCOCCOCCOCCOCCOC1.C1COCC1>[CH2:7]([O:14][C:15]1[CH:16]=[CH:17][C:18]([Br:23])=[C:19]([CH:20]=[CH2:1])[CH:22]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 2

HCID 108700245-(Benzyloxy)-2-bromobenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 692072164-(Benzyloxy)-1-bromo-2-vinylbenzene収率 86.5%

試薬・触媒・溶媒 3

HCID 2855718-Crown-6触媒HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyltriphenylphosphonium bromide (12.4 g, 0.0347 mol) and 18-crown-6 (90 mg, 0.41 mmol) were added to THF (100 mL). The mixture was cooled in a ice-water bath. Potassium tert-butoxide (34.7 mL of 1.0M in THF, 0.0347 mol) was added via cannula to the stirred solution. 5-(Benzyloxy)-2-bromobenzaldehyde (9.2 g, 0.0316 mol) was added in one portion which resulted in a slight exotherm. After 30 minutes the cooling bath was removed and stirring was continued at 22° C. for 5 hours. The mixture was concentrated and the residue was purified by flash column chromatography on SiO2 (75 g) with hexanes/ethyl acetate (95:5) to provide 4-(benzyloxy)-1-bromo-2-vinylbenzene as a clear oil (7.9 g, 86% yield). 1H NMR (300 MHz, CDCl3) δ 5.03 (s, 2H), 5.32 (d, J=10.98 Hz, 2H,) 5.63 (d, J=17.20 Hz, 2H), 6.74 (dd, J=8.78, 2.93 Hz, 2H), 6.98 (dd, J=17.57, 10.98 Hz, 2H), 7.13 (d, J=2.93 Hz, 2H), 7.33 (m, 6H).

後処理

  1. temperatureThe mixture was cooled in a ice-water bath
  2. customresulted in a slight exotherm
  3. customAfter 30 minutes the cooling bath was removed
  4. concentrationThe mixture was concentrated
  5. customthe residue was purified by flash column chromatography on SiO2 (75 g) with hexanes/ethyl acetate (95:5)

出典と根拠

ORDレコード
ord-14b84c4dfcab448582096ef09318d304
出典データセット
uspto-grants-2006_12
特許番号
US07153848B2

反応ノート

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