Ammonia → 3-bromo-4-methoxybiphenyl

HRID 1796888Notes

Reaction equation

HRID 1796888 reaction equation
COS([O:6][CH3:7])(=O)=O.[Br:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1O.[OH-].[Na+].N>O>[Br:8][C:9]1[CH:10]=[C:11]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:12]=[CH:13][C:14]=1[O:6][CH3:7]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 272972-Bromo-4-phenylphenol

Product 1

HCID 2622673-bromo-4-methoxybiphenyl

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Dimethylsulfate (10.3 mL, 109 mmol) was added to a mixture of 3-bromo-[1,1′-biphenyl]-4-ol and sodium hydroxide (8 g, 201 mmol) in water (12.4 mL) at 0° C. After stirring for 2 hours at reflux, ammonia (1.2 mL) was added to the mixture. The solid was filtered and washed with water. The product, 3-bromo-4-methoxy-1,1′-biphenyl, was crystallized from heptane.

Workup

  1. temperatureat reflux
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customThe product, 3-bromo-4-methoxy-1,1′-biphenyl, was crystallized from heptane

Sources & evidence

ORD record
ord-dfe7adf6f4ea4d8081037c68bb3f7edc
Source dataset
uspto-grants-2006_04
Patent number
US07033681B2

Reaction notes

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