Diethyl Ether → HCID 57532152, compound

HRID 1455234Notes

Reaction equation

HRID 1455234 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH2:7][CH2:8]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30].CCOCC>C1COCC1>[Br:30][CH2:8][CH2:7][C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 63967770553653-39-7

Product 1

HCID 57532152HCID 57532152, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of 2-(5-chloro-2-thienyl)-ethanol* (12.2 g) and triphenylphosphine (21.4 g) in anhydrous THF (150 ml) at 0° C. was added carbon tetrabromide (27.5 g). The reaction was stirred at 5° C. for 15 min then at room temperature for 2.5 h. Ether was added and the reaction was then filtered and the filtrate concentrated. The resultant residue was purified by flash column chromatography (silica, eluting with cyclohexane:DCM 8:1) to give the title compound (15 g) as an oil. * Schick et al., J. Amer. Chem. Soc., 70, 1948, 1646.

Workup

  1. waitat room temperature for 2.5 h
  2. filtrationthe reaction was then filtered
  3. concentrationthe filtrate concentrated
  4. customThe resultant residue was purified by flash column chromatography (silica, eluting with cyclohexane:DCM 8:1)

Sources & evidence

ORD record
ord-788361501b464294b3ac18cc90811c8f
Source dataset
uspto-grants-2009_01
Patent number
US07482374B2

Reaction notes

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