Bromocyclopentane → Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate

HRID 62712

反応式

HRID 62712 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].Br[CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:13])[C:11]=1[O:12][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)[C:5]([O:7][CH3:8])=[O:6]

参加物

5

反応物 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 76856Methyl 3,5-dichloro-4-hydroxybenzoate

生成物 1

HCID 67041559Methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate収率 84.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

Methyl 3,5-dichloro-4-hydroxybenzoate (1) (1.00 g, 4.52 mmol) was dissolved in DMF (8 mL) and treated with bromocyclopentane (534 μL, 4.98 mmol), followed by potassium carbonate (937 mg, 6.79 mmol). The mixture was stirred at 80° C. for 3 h and then partitioned between EtOAc (100 mL) and H2O (100 mL). The aqueous phase was extracted with EtOAc (50 mL) and the combined organic phases washed successively with water (5×50 mL) and brine (50 mL), then dried over MgSO4 and filtered. The solvent was removed in vacuo to afford methyl 3,5-dichloro-4-(cyclopentyloxy)benzoate (2) (1.10 g, 84%): 1H NMR (400 MHz, CDCl3) δ: 7.97 (2H, s), 5.04 (1H, m), 3.90 (3H, s), 2.04-1.91 (4H, m), 1.82-1.75 (2H, m), 1.69-1.60 (2H, m).

後処理

  1. custompartitioned between EtOAc (100 mL) and H2O (100 mL)
  2. extractionThe aqueous phase was extracted with EtOAc (50 mL)
  3. washthe combined organic phases washed successively with water (5×50 mL) and brine (50 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-1ce85cf82a9243398065a499278f6629
出典データセット
uspto-grants-2016_09
特許番号
US09447028B2

関連ノート

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