Benzyl Bromide → 5-(Benzyloxy)-2-bromobenzonitrile

HRID 1850725ノート

反応式

HRID 1850725 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[C:9]#[N:10].C([O-])([O-])=O.[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C=O)C.O>[CH2:17]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH:4]=1)[C:9]#[N:10])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 153231112-Bromo-5-hydroxybenzonitrile

生成物 1

HCID 121019865-(Benzyloxy)-2-bromobenzonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

4-bromo-3-cyanophenol (1 g, 5.05 mmol) was dissolved in DMF (10 ml) and K2CO3 (1.40 g, 10.10 mmol) and benzyl bromide (0.66 ml, 5.56 mmol) added. The mixture was stirred under N2 for 1 hr at RT. The mixture was diluted with water (15 mL) and extracted with EtOAc (2×10 mL). The organic fractions were combined, washed with brine (saturated, 1×8 mL), dried over MgSO4, filtered and the volatiles removed in vacuo. The residue was purified by chromatography on silica gel Biotage 25M, using a gradient eluant of EtOAc/Hexane (0-50%) to afford the title compound. LC/MS (m/z): 289 (M+H)+.

後処理

  1. extractionextracted with EtOAc (2×10 mL)
  2. washwashed with brine (saturated, 1×8 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe volatiles removed in vacuo
  6. customThe residue was purified by chromatography on silica gel Biotage 25M

出典と根拠

ORDレコード
ord-f4ebb45edb8e4e43989e82cd627d0888
出典データセット
uspto-grants-2015_02
特許番号
US08957062B2

反応ノート

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