Carbon tetrabromide → Diethyl 5-(Bromomethyl)isophthalate

HRID 899457Notes

Reaction equation

HRID 899457 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:6]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:8]=1.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH2:17]([O:16][C:14]([C:5]1[CH:4]=[C:3]([CH2:2][Br:20])[CH:8]=[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=1)=[O:15])[CH3:18]

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 610139Diethyl 5-(hydroxymethyl)isophthalate

Product 1

HCID 10935954Diethyl 5-(Bromomethyl)isophthalate

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of diethyl 5-(hydroxymethyl)benzene-1,3-dioate (3.5 g, 0.014 mol) and carbon tetrabromide (5.0 g, 0.015 mol) in 30 mL CH2Cl2, cooled to 0° C., was added dropwise a solution of triphenylphosphine (3.9 g, 0.015 mol) in 20 mL CH2Cl2. The reaction was stirred at 0° C. for 1.5 h, diluted with CHCl3, and washed with water and brine. Drying, solvent evaporation and flash chromatography (silica gel, 0-30% EtOAc/hexanes) gave diethyl-5-(bromomethyl)benzene-1,3-dioate. 1H NMR (400 MHz, CDCl3) δ 8.61 (s, 1H), 8.25 (app d, J=1.6 Hz, 2H), 4.55 (s, 2H), 4.42 (q, J=7.1 Hz, 4H), 1.42 (t, J=7.1 Hz, 6H).

Workup

  1. washwashed with water and brine
  2. customDrying
  3. customsolvent evaporation and flash chromatography (silica gel, 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7077a024afe041eebc83fbc1322138dc
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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