Hydrogen Bromide → Tributyl(3-oxo-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl)phosphonium bromide

HRID 925061Notes

Reaction equation

HRID 925061 reaction equation
O[CH:2]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=2[C:4](=[O:11])[O:3]1.[CH2:12]([P:16]([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].[BrH:25]>C(O)(=O)C>[Br-:25].[CH2:21]([P+:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[CH:2]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:5]=2[C:4](=[O:11])[O:3]1)[CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 13831TributylphosphineHCID 109097774,5,6,7-Tetrahydro-3-hydroxy-1(3H)-isobenzofuranone

Product 1

HCID 66966753Tributyl(3-oxo-1,3,4,5,6,7-hexahydro-2-benzofuran-1-yl)phosphonium bromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of EXAMPLE 1A (3 g) in acetic acid (10 mL) at ambient temperature was treated with tri-n-butyl phosphine (4.81 mL) and 33% hydrobromic acid in acetic acid (3.34 mL), heated at reflux for 21 hours, cooled and concentrated. The concentrate was purified by flash chromatography on silica gel with 10% methanol in dichloromethane.

Workup

  1. temperatureheated
  2. temperatureat reflux for 21 hours
  3. temperaturecooled
  4. concentrationconcentrated
  5. customThe concentrate was purified by flash chromatography on silica gel with 10% methanol in dichloromethane

Sources & evidence

ORD record
ord-b531f3878562488991cab57885e0b601
Source dataset
uspto-grants-2016_03
Patent number
US09283222B2

Reaction notes

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