Carbon tetrabromide → Methyl (4-bromomethyl-2-propylphenoxy)-2-phenylacetate

HRID 257837Notes

Reaction equation

HRID 257837 reaction equation
O[CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1.C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:25][CH2:2][C:3]1[CH:20]=[CH:19][C:6]([O:7][CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([O:11][CH3:12])=[O:10])=[C:5]([CH2:21][CH2:22][CH3:23])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19802778Methyl (4-hydroxymethyl-2-propylphenoxy)-2-phenylacetate

Product 1

HCID 19781781Methyl (4-bromomethyl-2-propylphenoxy)-2-phenylacetateYield 80.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred (0° C.) solution of 0.750 g (2.31 mmol) of the product of Step G, and 0.949 g (2.86 mmol) of carbon tetrabromide dissolved in 7 mL of methylene chloride was added 0.751 g of triphenylphosphine (2.86 mmol) in portions. After the addition was complete, the reaction mixture was stirred and allowed to warm to room temperature over 1 hour. The reaction mixture was then evaporated in vacuo, and the residue was purified on a silica gel flash chromatography column eluted with 10% ethyl acetate/hexane to afford 0.703 g (78%) of the title compound.

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was then evaporated in vacuo
  3. customthe residue was purified on a silica gel flash chromatography column
  4. washeluted with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d169c8c87d5742f7b4fccdfcb7dd6f98
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Reaction notes

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