Potassium Carbonate → 9-Bromomethylanthracene

HRID 2061370

反応式

HRID 2061370 の反応式
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15]O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.P(Br)(Br)[Br:18].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[Br:18][CH2:15][C:13]1[C:14]2[C:5]([CH:6]=[C:7]3[C:12]=1[CH:11]=[CH:10][CH:9]=[CH:8]3)=[CH:4][CH:3]=[CH:2][CH:1]=2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 738489-Anthracenemethanol

生成物 1

HCID 170199-Bromomethylanthracene収率 54%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

To a stirring suspension of 9-anthracenemethanol (2.0 g, 9.6 mmol) at 0° C. in toluene (100 ml) was added PBr3 (1.2 mL, 12.51 mmol) and the suspension was stirred at 0° C. for 1 h. The reaction mixture was then brought up to room temperature and let to stir for further 1 h. The mixture turned into a yellow solution. K2CO3 (10 mL) was added to quench the reaction. Toluene was evaporated off in-vacuo. The residue was taken up in EtOAc and washed with saturated aqueous K2CO3, water and brine and dried (MgSO4). The solvent was evaporated off in-vacuo and the crude residue was purified by flash chromatography, eluting with hexane:EtOAc (2:1) to give 47 (1.4 g, 54%) as yellow solid. H1 NMR (500 MHz, CDCl3): δ=8.45 (1H, s, Ar-10H), 8.27 (2H, d, Ar-1, 8H), 8.00 (2H, d, Ar-4, 6H), 7.62 (2H, d, Ar-2, 7H), 7.48 (2H, d, Ar-3, H), 5.50 (2H, s, CH2).

後処理

  1. customwas then brought up to room temperature
  2. stirringto stir for further 1 h
  3. customto quench
  4. customthe reaction
  5. customToluene was evaporated off in-vacuo
  6. washwashed with saturated aqueous K2CO3, water and brine
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated off in-vacuo
  9. customthe crude residue was purified by flash chromatography
  10. washeluting with hexane:EtOAc (2:1)

出典と根拠

ORDレコード
ord-1c3d13e096ba48898c9acdd18943c071
出典データセット
uspto-grants-2012_10
特許番号
US08283340B2

関連ノート

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