Ammonium Chloride → 3,5-Dibromostyrene

HRID 2380751ノート

反応式

HRID 2380751 の反応式
[CH3:1]C(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Br:16])[CH:15]=1)[CH:11]=O.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([Br:16])[CH:15]=1)[CH:11]=[CH2:1]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 6220773,5-DibromobenzaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 186903433,5-Dibromostyrene収率 79.3%

試薬・触媒・溶媒 2

HCID 74505Methyltriphenyliphosphonium bromide触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Tetrahydrofuran (20 mL) was added to methyltriphenylphosphonium bromide (3.150 g, 8.8 mmol). Then potassium t-butoxide (0.989 g, 8.8 mmol) was added herein small portions with ice-cooling, and the mixture was stirred at room temperature for 1 hr. The resultant slurry was cooled to −78° C. and a tetrahydrofuran (20 mL) solution containing 3,5-dibromobenzaldehyde (1.519 g, 5.8 mmol) was added dropwise. The reaction solution was allowed to warm to room temperature and stirred for 1 hr, and then a saturated ammonium chloride aqueous solution was added to the reaction solution. The product was extracted with ethyl acetate, the solvent was distilled off under reduced pressure, and the residue was purified with silica-gel column chromatography to obtain 3,5-dibromostyrene (1.2 g, 4.6 mmol).

後処理

  1. temperaturecooling
  2. temperatureThe resultant slurry was cooled to −78° C.
  3. additionwas added dropwise
  4. temperatureto warm to room temperature
  5. stirringstirred for 1 hr
  6. extractionThe product was extracted with ethyl acetate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customthe residue was purified with silica-gel column chromatography

出典と根拠

ORDレコード
ord-d1ff980968f943d1a2170927d015c4c1
出典データセット
uspto-grants-2012_09
特許番号
US08257837B2

反応ノート

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