Carbon tetrabromide → tert-Butyl 3-(bromomethyl)phenylcarbamate

HRID 1616167

反応式

HRID 1616167 の反応式
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14]O)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:37]>ClCCl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][Br:37])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 14523557tert-Butyl (3-(hydroxymethyl)phenyl)carbamate

生成物 1

HCID 14523558tert-Butyl 3-(bromomethyl)phenylcarbamate収率 71.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl[3-(hydroxymethyl)phenyl]carbamate (0.90 g, 4.0 mmol) in dichloromethane (15 mL) cooled at 0° C. was added triphenylphosphine (1.59 g, 6.05 mmol) and carbon tetrabromide (2.01 g, 6.05 mmol) and the reaction was stirred at rt overnight. The reaction was quenched with water and extracted with DCM (2×). The combined organic phases were then washed with water, and brine, dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by flash silica gel chromatography (0% to 20% EtOAc/hexanes) to afford tert-butyl[3-(bromomethyl)phenyl]carbamate (0.82 g, 70%). LC-MS: (FA) ES+ 271.

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with DCM (2×)
  3. washThe combined organic phases were then washed with water, and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash silica gel chromatography (0% to 20% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-6f3da6370e4c4d2e9cd49559445134a6
出典データセット
uspto-grants-2014_07
特許番号
US08765773B2

関連ノート

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