Phosphorus tribromide → HCID 86605565, compound

HRID 1819960Notes

Reaction equation

HRID 1819960 reaction equation
[CH2:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([CH2:18]O)=[C:14]([CH3:20])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2].P(Br)(Br)[Br:22]>C1COCC1>[Br-:22].[CH2:1]([C:3]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:20])[CH:13]=1)([C:6]1[S:7][CH:8]=[C:9]([CH3:11])[CH:10]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 57890157HCID 57890157, compound

Product 1

HCID 86605565HCID 86605565, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methanol (6 g,) in THF (50 ml) is treated with PBr3 (2.2 ml, 23.3 mmol) and warmed to RT. After stirring for 2 h, the mixture is partitioned between EtOAc and brine. The organic layer is MgSO4 dried, concentrated, and dissolved in anhydrous THF (30 ml) to give a solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methane bromide. Separately, a solution of 3,3-dimethyl-butan-2-one (5.3 ml, 42.4 mmol) in THF (15 ml) is treated with LiHMDS (42.4 ml, 42.4 mmol, 1M in THF) at −70° C. for 1 h. This solution is transferred (via cannula) into a −70° C. solution of {4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenyl}-methanebromide/THF. The mixture is warmed to RT and stirred for 1 h. The reaction is diluted with EtOAc and washed with 0.2 N HCl until the aq layer is pH 2. The organic layer is concentrated to give the title compound (6.2 g, 79%).

Workup

  1. customthe mixture is partitioned between EtOAc and brine
  2. customdried
  3. concentrationconcentrated
  4. dissolutiondissolved in anhydrous THF (30 ml)

Sources & evidence

ORD record
ord-ba647541c1984f15aacd342012d78a66
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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