4-Nitrophenol → 2-Bromo-4-nitrophenol

HRID 858274Notes

Reaction equation

HRID 858274 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClCCl.[Br:14]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Fe].O>[Br:14][C:8]1[CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[OH:10]

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 6344DichloromethaneHCID 24408BromineHCID 24477Sodium Thiosulfate

Product 1

HCID 221092-Bromo-4-nitrophenol

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

139.40 g (64.7 mmol) of 4-nitrophenol and 130 ml of dichloromethane are introduced into a three-necked flask under an argon atmosphere. The mixture is cooled to 0° C. and 3.31 ml (67.7 mmol) of bromine are added dropwise. The reaction medium is stirred for one hour at 0° C., 360 mg (6.5 mmol) of iron powder are then added and this mixture is stirred for sixteen hours at room temperature. The reaction medium is poured into water, a saturated sodium thiosulphate solution is added, this mixture is extracted with dichloromethane and washed with water, the organic phase is separated out after settling has taken place and dried over magnesium sulphate, and the solvents are evaporated off. 13.50 g (96%) of the expected compound are collected in the form of a beige-coloured powder with a melting point of 105–107° C.

Workup

  1. stirringthis mixture is stirred for sixteen hours at room temperature
  2. extractionthis mixture is extracted with dichloromethane
  3. washwashed with water
  4. customthe organic phase is separated out after settling
  5. dry with materialdried over magnesium sulphate
  6. customthe solvents are evaporated off
  7. custom13.50 g (96%) of the expected compound are collected in the form of a beige-coloured powder with a melting point of 105–107° C.

Sources & evidence

ORD record
ord-9dd5d92796dc4eecab79753f83113cb8
Source dataset
uspto-grants-2006_12
Patent number
US07148245B2

Reaction notes

Loading…