Triphenylphosphine → Benzene, ((2-bromoethoxy)methyl)-

HRID 1842926Notes

Reaction equation

HRID 1842926 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:38])C(=O)C1>C(Cl)Cl>[Br:38][CH2:10][CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 121412-(Benzyloxy) ethanolHCID 67184N-bromobutanimide

Product 1

HCID 73833Benzene, ((2-bromoethoxy)methyl)-Yield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-(benzyloxy)ethanol (17.0 g, 111.84 mmol) and PPh3 (35.0 g, 134.21 mmol) in DCM (170 mL) at −10° C. to −5° C., NBS (23.88 g, 134.21 mmol) was added slowly in portions maintaining the temperature at −10° C. to −5° C. After addition, the reaction mixture was allowed to stir at RT for 1 h until complete consumption starting material, as evidenced by TLC analysis. The reaction mixture was concentrated, the obtained crude compound was purified by CC using 5% EtOAc in PE as eluent to afford ((2-bromoethoxy)methyl)benzene (13.5 g, 56.2%) as pale yellow liquid (TLC solvent system: 30% EtOAc in PE; Rf: 0.7).

Workup

  1. temperaturemaintaining the temperature at −10° C. to −5° C
  2. additionAfter addition
  3. concentrationThe reaction mixture was concentrated
  4. customthe obtained crude compound
  5. customwas purified by CC

Sources & evidence

ORD record
ord-4484467d2d1b4054885cabf672dd7c21
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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