Phosphorus tribromide → 2-(Bromomethyl)-1-iodo-4-(trifluoromethyl)benzene

HRID 1270794Notes

Reaction equation

HRID 1270794 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([I:11])=[C:7]([CH:10]=1)[CH2:8]O.P(Br)(Br)[Br:15]>CCOCC>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]([I:11])=[C:7]([CH:10]=1)[CH2:8][Br:15]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 23160665(2-Iodo-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 184515342-(Bromomethyl)-1-iodo-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-Trifluoromethyl-2-iodobenzyl alcohol (45 g, 0.15 mol) is dissolved in anhydrous Et2O (400 mL) and treated with phosphorous tribromide (41 mL, 0.15 mol) by dropwise addition. The reaction mixture is stirred at room temperature overnight and quenched by slow addition of water (150 mL). The organic layer is separated, washed with saturated aqueous NaHCO3 (250 mL), brine (250 mL), dried (MgSO4) and concentrated by rotary evaporator to give 5-trifluoromethyl-2-iodobenzyl bromide as an oil.

Workup

  1. customquenched by slow addition of water (150 mL)
  2. customThe organic layer is separated
  3. washwashed with saturated aqueous NaHCO3 (250 mL), brine (250 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-1a5d81503e994efba0ee91ba2bb611a6
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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