Carbon tetrabromide → Methyl 2-(bromomethyl)-4,5-dichlorobenzoate

HRID 1681945Notes

Reaction equation

HRID 1681945 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([Cl:10])[C:7]([Cl:11])=[CH:6][C:5]=1[CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C(Cl)Cl>[Br:35][CH2:12][C:5]1[CH:6]=[C:7]([Cl:11])[C:8]([Cl:10])=[CH:9][C:4]=1[C:3]([O:2][CH3:1])=[O:14]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19804259Methyl-4,5-dichloro-2-(hydroxymethyl)benzoate

Product 1

HCID 19804260Methyl 2-(bromomethyl)-4,5-dichlorobenzoateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 169 mg (0.72 mmol) of the product of Step B in 3 mL of CH2Cl2 at 0° C. was added 283 mg (1.08 mmol, 1.5 eq) of triphenylphosphine and 360 mg (1.08 mmol, 1.5 eq) of carbon tetrabromide. The mixture was stirred for 16 hours and quenched with methanol. The reaction was concentrated in vacuo and the resultant oil was flash chromatographed with 2:1 hexane/ethyl acetate to afford the titled compound (107 mg, 50%) as a brownish orange oil.

Workup

  1. customquenched with methanol
  2. concentrationThe reaction was concentrated in vacuo
  3. customchromatographed with 2:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-419fdd495a0347adb6b5517310cd4e52
Source dataset
uspto-grants-1992_12
Patent number
US05175164

Reaction notes

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