4-Bromophenol → 1-Bromo-4-(methoxymethoxy)benzene

HRID 222072Notes

Reaction equation

HRID 222072 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH3:9][O:10][CH2:11]OC.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][O:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 8020DimethoxymethaneHCID 14812Phosphorus oxide (P4O10)

Product 1

HCID 104659191-Bromo-4-(methoxymethoxy)benzeneYield 57.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromophenol (0.50 g, 2.89 mmol) and dimethoxymethane (2.6 mL, 29.39 mmol) in DCM (60 mL) was added P2O5 (1.50 g, 10.57 mmol). The reaction mixture was stirred at for 1 h and insoluble precipitate was filtered off. Solid Na2CO3 was added to the solution and stirred for additional 10 min. The solid was filtered off and the solution was concentrated. Purification on a silica gel column gave the desired product as a clear oil (363 mg). NMR (CDCl3): 7.38 (d, 2H), 6.93 (d, 2H), 5.15 (s, 2H), 3.47 (s, 3H).

Workup

  1. filtrationwas filtered off
  2. additionSolid Na2CO3 was added to the solution
  3. stirringstirred for additional 10 min
  4. filtrationThe solid was filtered off
  5. concentrationthe solution was concentrated
  6. customPurification on a silica gel column

Sources & evidence

ORD record
ord-116db555946d4209aa66ef0278629dfe
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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