Catechol → 4-Bromocatechol

HRID 442638

Reaction equation

HRID 442638 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].[Br-:9].[Br-].O1CCOCC1>CCOCC>[Br:9][C:6]1[CH:5]=[C:3]([OH:4])[C:1](=[CH:8][CH:7]=1)[OH:2]

Participants

4

Reactant 2

HCID 289CatecholHCID 222259191,4-Dioxane dibromide

Product 1

HCID 284874-Bromocatechol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Catechol (11.0 g; 0.100 mol) is dissolved in 50 ml of ether and 29 g of freshly-prepared dioxane dibromide (Yanovskaya, Terent'ev and Belsn'kii), J. Gen. Chem. Vol. 22:1594 (1952)) is added slowly as a solution in 50 ml of ether. The organic solution is washed with water (3 times) and dried over MgSO4. The solvent is removed under reduced pressure to yield 4-bromocatechol as a red-brown oil. 1H NMR δ 5.52 (s, 1), 5.70 (s, 1), 6.74 (d, 1, J=8.74 Hz), 6.92 (dd, 1, J=8.3, 2.3 Hz), and 7.01 ppm (d, 1, J=2.6 Hz).

Workup

  1. washThe organic solution is washed with water (3 times)
  2. dry with materialdried over MgSO4
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7a8cd17ab38f4cae84e9d2c009d1aeba
Source dataset
uspto-grants-1999_04
Patent number
US05891876

Linked notes

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