1,2,3-Tribromobenzene → 5-Bromo-9-isopropylidene-1,4-dihydro-1,4-methano-naphthalene

HRID 39409

반응식

HRID 39409 반응식
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](Br)[C:3]=1[Br:9].[CH3:10][C:11]([CH3:17])=[C:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.C([Li])CCC.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[Br:9][C:3]1[CH:2]=[CH:7][CH:6]=[C:5]2[C:4]=1[CH:13]1[C:12](=[C:11]([CH3:17])[CH3:10])[CH:16]2[CH:15]=[CH:14]1

참가 물질

6

반응물 4

HCID 118421,2,3-TribromobenzeneHCID 25517Ammonium ChlorideHCID 1374671,3-Cyclopentadiene, 5-(1-methylethylidene)-HCID 178418339Butyllithium

생성물 1

HCID 578576055-Bromo-9-isopropylidene-1,4-dihydro-1,4-methano-naphthalene수율 66%

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

To a stirred solution of 1,2,3-tribromo-benzene (4.34 g, 13.8 mmol) and 6,6-dimethylfulvene (2.38 g, assay 92.6%, 20.7 mmol) in dry toluene (60 ml) under a nitrogen atmosphere, 5.5 ml of a 2.5M toluene solution of n-butyllithium (14.5 mmol) were added dropwise at −5 to 0° C. within 10 minutes. After a further 10 minutes at 0° C. and 2 hours at ambient temperature, the reaction mixture was poured onto a saturated aqueous solution of ammonium chloride, extracted with ethyl acetate, washed with brine and water, dried over sodium sulphate and evaporated. Purification of the crude material on silca gel in hexane afforded 2.38 g of the desired product as a yellow oil (assay 84% by g.l.c., 55% yield). This reaction is also disclosed in WO 2007/068417.

후처리

  1. extractionextracted with ethyl acetate
  2. washwashed with brine and water
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customPurification of the crude material on silca gel in hexane

출처 및 근거

ORD 기록
ord-bc797f142524417b8cd33e6edb8dedf8
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524915B2

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