1,2-Dibromoethane → Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

HRID 858592

반응식

HRID 858592 반응식
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1.[H-].[Na+].Br[CH2:16][CH2:17]Br>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]([C:4]1([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=2)[CH2:17][CH2:16]1)=[O:12]

참가 물질

6

반응물 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 11746402Methyl 2-(3-bromophenyl)acetate

생성물 1

HCID 58762755Methyl 1-(3-bromophenyl)cyclopropane-1-carboxylate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of (3-Bromo-phenyl)-acetic acid methyl ester (4.54 g, 20 mmol) dissolved in dry THF (10 mL) was added dropwise to suspension of NaH (95% dry, 1.05 g, 44 mmol) in DMF (40 mL) and THF (10 mL), under a nitrogen atmosphere, at 0° C. After 30 min, gas evolution ceased, and 1,2-dibromoethane (3.79 mL, 44 mmol) was added dropwise over 20 min. The resulting mixture was stirred for 1 h, then quenched with 1N HCl, extracted with ether, washed with brine, dried over MgSO4, and stripped of solvent. The resulting oil was distilled under high vacuum. The product was collected between 95° C. and 105° C. Yield 2 g, 39%.

후처리

  1. customquenched with 1N HCl
  2. extractionextracted with ether
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. distillationThe resulting oil was distilled under high vacuum
  6. customThe product was collected between 95° C. and 105° C

출처 및 근거

ORD 기록
ord-cade5ce11673478f85747444370f5d82
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07148226B2

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