Boron tribromide → 4-Chloro-2-iodophenol

HRID 2220224Notes

Reaction equation

HRID 2220224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[C:4]([I:10])[CH:3]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([I:10])[CH:3]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 28009784-Chloro-2-iodoanisole

Product 1

HCID 6202344-Chloro-2-iodophenolYield 88.7%

Conditions

Temperature
0 °C

Procedure

To 4-Chloro-2-iodo-1-methoxy-benzene (5.00 g, 18.6 mmol) in an ice bath under argon was added dropwise neat BBr3 (2.20 mL, 23.2 mmol). This mixture was stirred at 0° C. for 3.5 hours and then quenched with MeOH (20 mL). This mixture was concentrated in vacuo to give 4.2 g of 4-Chloro-2-iodo-phenol in 88% yield. HPLC Rt=3.17 min (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. customquenched with MeOH (20 mL)
  2. concentrationThis mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-e87149398414430f8586b43b65f58965
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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