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

HRID 1459690Notes

Reaction equation

HRID 1459690 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]N1C(=O)CCC1=O.[CH2:28]([O:35][CH2:36][CH2:37]O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[CH2:28]([O:35][CH2:36][CH2:37][Br:20])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 121412-(Benzyloxy) ethanolHCID 67184N-bromobutanimide2×

Product 1

HCID 73833Benzene, ((2-bromoethoxy)methyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of triphenyl phosphine (2.1 g, 7.9 mmol) in dry methylene chloride (16 mL) was added dropwise over 10 min to a stirred mixture of N-bromosuccinimide (1.4 g, 7.9 mmol) in dry methylene chloride (23 mL) at -78° C. The reaction was kept in the dark and stirring was continued until all the N-bromosuccinimide had dissolved (10 min). A solution of 2-(benzyloxy)ethanol in dry methylene chloride (10 mL) was added dropwise. The cooling bath was removed and stirring was continued for 12 h at rt. The organic layer was then concentrated in vacuo and passed through a silica plug with 1:1 hexane:methylene chloride to afford 2-(benzyloxy)bromoethane (1.20 g, 85%).

Workup

  1. dissolutionhad dissolved (10 min)
  2. customThe cooling bath was removed
  3. stirringstirring
  4. concentrationThe organic layer was then concentrated in vacuo

Sources & evidence

ORD record
ord-df652ac02d4d40b0957e80d82fd535fb
Source dataset
uspto-grants-1998_12
Patent number
US05854277

Reaction notes

Loading…