Hydrochloric Acid → HCID 54508553, 화합물

HRID 265209노트

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HRID 265209 반응식
[F:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[Br-].[F:20][C:21]1[C:46]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[CH:45][CH:44]=[CH:43][C:22]=1[CH2:23][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].FC(O)C1C=CC=C(OCCCCCCCC)C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrBr.FC1C(OCCCCCCCC)=CC=CC=1CBr.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].Cl>C1COCC1.C1(C)C=CC=CC=1.O>[F:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:23][C:22]1[CH:43]=[CH:44][CH:45]=[C:46]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[C:21]=1[F:20]

참가 물질

13

반응물 9

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 15219970HCID 15219970, 화합물2회HCID 190337812-Fluoro-3-octyloxybenzyl bromideHCID 19033783HCID 19033783, 화합물HCID 21226445Aluminium lithium hydrideHCID 23665647Potassium tert-butoxideHCID 44191054Bromine triphenylphosphineHCID 54042522HCID 54042522, 화합물

생성물 1

HCID 54508553HCID 54508553, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매3회

실험 절차

A solution of 2.5 g of 2-fluoro-3-octyloxybenzaldehyde (prepared by reacting 2-octyloxyfluorobenzene with lithium diisopropylamide followed by reaction with N,N-dimethylformamide) in 50 ml of THF is added dropwise at 20° C. to a fully reacted mixture of 5.6 g of 2-fluoro-3-octyloxybenzyltriphenylphosphoniumbromide (prepared by the reaction sequence: reaction of 2-fluoro-3-octyloxybenzaldehyde with LiAlH4 in THF to give fluoro-3-octyloxybenzyl alcohol, reaction of the latter with triphenylphosphine/Br2 to give 2-fluoro-3-octyloxybenzyl bromide and reaction of the latter with triphenylphosphine in toluene) and 1.2 g of potassium tert-butoxide in 100 ml of THF. When the reaction is complete, the mixture is adjusted to pH 5 using HCl, 500 ml of H2O are added, and the mixture is extracted three times with 100 ml of diethyl ether in each case. Chromatography on silica gel using dichloromethane/heptane 1:1 gives 1,2-bis(2-fluoro-3-octyloxyphenyl)ethene as an E/Z-mixture. The latter is dissolved in cyclohexane, 4 mol % of iodine are added, and the mixture is exposed to UV light for 8 hours at 25° C. in a quartz apparatus. Chromatography on SiO2 using dichloromethane and recrystallization from acetonitrile give 1.2 g of 1,8-difluoro-2,7-dioctyloxyphenanthrene as colorless crystals.

후처리

  1. customprepared by the reaction sequence
  2. customto give
  3. customto give
  4. additionare added
  5. extractionthe mixture is extracted three times with 100 ml of diethyl ether in each case

출처 및 근거

ORD 기록
ord-9c2dc07ff3df4f9e9d427809f42eff4f
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05648021

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