Carbon tetrabromide → Tert-butyl 4-(2-bromoethyl)benzoate

HRID 1913772Notes

Reaction equation

HRID 1913772 reaction equation
Br[C:2]([Br:5])(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.OC[CH2:27][C:28]1[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:30][CH:29]=1>C1COCC1.O=O>[Br:5][CH2:2][CH2:27][C:28]1[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 10331132Tert-butyl 4-(2-hydroxyethyl)benzoate

Product 1

HCID 10803033Tert-butyl 4-(2-bromoethyl)benzoateYield 95.1%

Reagents, catalysts & solvents 2

HCID 977OxygenSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7.16 g (21.59 mmol) of tetrabromomethane and 5.66 g (21.59 mmol) of triphenylphosphine are dissolved in 70 ml of THF with exclusion of oxygen and stirred at room temperature for 30 minutes. Then 3.2 g (14.4 mmol) of tert-butyl 4-(2-hydroxyethyl)benzoate, dissolved in 30 ml of THF, are added dropwise, and the reaction mixture is stirred at room temperature for 12 hours. After conversion is complete, the mixture is evaporated to dryness and the resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1). 3.9 g (13.7 mmol, 87% yield) of the title compound are obtained as a colourless oil.

Workup

  1. additionare added dropwise
  2. stirringthe reaction mixture is stirred at room temperature for 12 hours
  3. customthe mixture is evaporated to dryness
  4. customthe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-2fd25e9577c64476bd1f945826d975c9
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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