Carbon Tetrachloride → 1-(Bromomethyl)-3-tert-butylbenzene

HRID 369796

反応式

HRID 369796 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH3:11])[CH:8]=[CH:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Br:12]N1C(=O)CCC1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>CCCCCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][Br:12])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 4

HCID 5943Carbon TetrachlorideHCID 7187Benzoyl PeroxideHCID 337113-tert-Butyltoluene2 回HCID 67184N-bromobutanimide

生成物 1

HCID 140976451-(Bromomethyl)-3-tert-butylbenzene収率 35%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser, a thermometer, and a magnetic stirrer was charged with 2.0 g of 3-tert-butyltoluene (Wiley Organics, Coshocton, Ohio 43812), 2.40 g of N-bromosuccinimide (Aldrich), and 30 mL of CCl4. The mixture was treated with 0.16 g of benzoyl peroxide (Aldrich) and heated at 6-° C. under N2. Careful temperature control is important to minimize by-product formation. After 1 h at 60° C. the reaction mixture was cooled to 0° C., filtered to remove succinimide, and the filtrate was concentrated in vacuo to afford a light yellow liquid. Analysis of this material by tlc (SiO2, hexane) indicated a major new component at Rf =0.50, a minor component at Rf =0.55, and a trace of 3-tert-butyltoluene at Rf =0.75. The crude product was purified by flash chromatography on 100 g of silica gel (hexane) to afford 1.06 g (35%) of 3-tert-butylbenzyl bromide as a clear liquid.

後処理

  1. customA dry 100 mL 3-necked flask equipped with a nitrogen inlet, a condenser
  2. temperatureheated at 6-° C
  3. filtrationfiltered
  4. customto remove succinimide
  5. concentrationthe filtrate was concentrated in vacuo
  6. customto afford a light yellow liquid
  7. customThe crude product was purified by flash chromatography on 100 g of silica gel (hexane)

出典と根拠

ORDレコード
ord-899c5ad1c9a44de4b6fb8f74dff97171
出典データセット
uspto-grants-2000_10
特許番号
US06140100

関連ノート

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