Carbon Tetrachloride → Triphenylphosphine

HRID 2102130Notes

Reaction equation

HRID 2102130 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH2:7]O)=[CH:4][CH:3]=1.[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(Cl)(Cl)[Cl:29]>>[Br:1][C:2]1[O:6][C:5]([CH2:7][Cl:29])=[CH:4][CH:3]=1.[C:22]1([P:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 14595701(5-Bromofuran-2-yl)methanol

Product 2

HCID 11776TriphenylphosphineHCID 122078912-Bromo-5-(chloromethyl)furan

Conditions

Temperature
75 °C

Procedure

To a solution of (5-bromo-2-furanyl)methanol (Example 310A) (144 mmol) in dry carbon tetrachloride (30 mL) was added triphenylphosphine (6.0 g, 228 mmol) at rt. The reaction is heated at 75° C. for 1 h. Concentration and purification by radial chromatography (0-10% EtOAc-hexanes gradient) afforded the title compound with contamination of triphenylphosphine. The product is used without further purification.

Workup

  1. concentrationConcentration and purification by radial chromatography (0-10% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-9259825253bb4a209bc5a916f4126286
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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