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Water → HCID 178419338, compound

HRID 425954
Notes
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Reaction equation

HRID 425954 reaction equation
[Li]CCCC.Br[C-:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.[C-:12]1([Br:17])[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:18].[Cl-].[CH:20]1([PH:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.O>C1COCC1.CCCCCC>[CH:27]1([P:26]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]2)[C-:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1.[Br:17][C-:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.[Fe+2:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 15181852DibromoferroceneHCID 21534679Dicyclohexylphosphane chlorideHCID 178418339Butyllithium

Product 1

HCID 178419338HCID 178419338, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

120 ml (0.3 mol) of n-BuLi (2.5 M in hexane) are added dropwise to a solution of 103 g (0.3 mol) of 1,1′-dibromoferrocene in 300 ml of THF at a temperature of <−30° C. The mixture is stirred at this temperature for a further 1.5 hours. It is then cooled to −50° C. and 66.2 ml (0.3 mol) of dicyclohexylphosphine chloride are added dropwise at such a rate that the temperature does not exceed −45° C. After stirring the mixture for a further 10 minutes, the temperature is allowed to rise to room temperature and the mixture is stirred for another one hour. After addition of 150 ml of water, the reaction mixture is shaken with hexane. The organic phases are dried over sodium sulphate and the solvent is distilled off under reduced pressure on a rotary evaporator. The residue is crystallized in ethanol. The product A2 is obtained in a yield of 84% (yellow solid). 1H NMR (300 MHz, C6D6): δ 1.20-2.11 (m, 22H), 3.97 (m, 2H), 4.23 (m, 2H), 4.26 (m, 2H), 4.41 (m, 2H). 31P NMR (121.5 MHz, C6D6): δ −8.3 (s).

Workup

  1. customdoes not exceed −45° C
  2. stirringAfter stirring the mixture for a further 10 minutes
  3. customto rise to room temperature
  4. stirringthe mixture is stirred for another one hour
  5. dry with materialThe organic phases are dried over sodium sulphate
  6. distillationthe solvent is distilled off under reduced pressure on a rotary evaporator
  7. customThe residue is crystallized in ethanol

Sources & evidence

ORD record
ord-910f85ab9c3849d39f3403380e2ce8c9
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08106227B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes