Carbon tetrabromide → Ethyl [4-(bromomethyl)-2-methylphenoxy]acetate

HRID 1269598Notes

Reaction equation

HRID 1269598 reaction equation
O[CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1.[Br:17]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:17][CH2:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:5]([CH3:16])[CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 58622858Ethyl [4-(hydroxymethyl)-2-methylphenoxy]acetate

Product 1

HCID 58622841Ethyl [4-(bromomethyl)-2-methylphenoxy]acetateYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl [4-(hydroxymethyl)-2-methylphenoxy]acetate (4.27 g, 19 mmol) in dry CH2Cl2 (150 mL) under nitrogen at 5° C., was added tetrabromomethane (6.91 g, 20.9 mmol) then triphenylphosphine (5.71 g, 21.8 mmol) portion wise over 0.5 h. The resultant mixture was then stirred for 16 h at room temperature. The solvents were removed in vacuo. Purification by Biotage™ chromatography (silica, 2×90 g) eluting with 30:1 cyclohexane:EtOAc afforded the title compound as a yellow solid (2.95 g).

Workup

  1. customThe solvents were removed in vacuo
  2. customPurification by Biotage™ chromatography (silica, 2×90 g)
  3. washeluting with 30:1 cyclohexane

Sources & evidence

ORD record
ord-2861707c1fd94c18b32a3157b08360d2
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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