Carbon tetrabromide → 4-Bromomethylphthalic acid dimethyl ester

HRID 2307588Notes

Reaction equation

HRID 2307588 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].[Br:17]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:17][CH2:2][C:3]1[CH:4]=[C:5]([C:13]([O:15][CH3:16])=[O:14])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22345632Dimethyl 4-hydroxymethylphthalate

Product 1

HCID 232556044-Bromomethylphthalic acid dimethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

36 g (176 mmol) of dimethyl 4-hydroxymethylphthalate are dissolved in 300 mL of dichloromethane and 70 g (211 mmol) of tetrabromomethane are added. A solution of 55.3 g (211 mmol) of triphenylphosphine in 200 mL of dichloromethane is then added slowly and the reaction mixture is stirred for 3 h at room temperature. After treatment with water and extraction with dichloromethane, the residue is purified by chromatography on a column of silica (eluent: dichloromethane). The desired product is obtained in the form of a colourless oil (m=25 g; Y=50%).

Workup

  1. extractionAfter treatment with water and extraction with dichloromethane
  2. customthe residue is purified by chromatography on a column of silica (eluent: dichloromethane)

Sources & evidence

ORD record
ord-f3d20a93b8a7459d982a495cd0c60584
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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