Hydrochloric Acid → 1-Bromo-3-methoxy-5-methylbenzene

HRID 1035587Notes

Reaction equation

HRID 1035587 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[C:5](N)=[C:4]([O:10][CH3:11])[CH:3]=1.Cl.N([O-])=O.[Na+].P(P(O)(O)=O)(O)(O)=O>C(O)(=O)C.O>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24536Hypophosphoric acidHCID 106802184-Bromo-2-methoxy-6-methylanilineHCID 23668193Sodium Nitrite

Product 1

HCID 106795541-Bromo-3-methoxy-5-methylbenzene

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

The reaction is performed in a water/ice bath. 500 mg (2.31 mmol, 1 eq) of 4-bromo-2-methoxy-6-methylaniline is dissolved in a mixture of 7 ml of acetic acid and 3 ml of water, followed by adding 0.8 ml of concentrated hydrochloric acid (37%) and 207 mg (3.00 mmol, 1.5 eq) of sodium nitrite dissolved in 1 ml of water. The mixture is stirred for 30 min and subsequently added to 8 ml of ice-cooled 50% by weight hypophosphoric acid. The reaction is stirred at 0° C. for 8 hours and allowed to stand at RT over night.

Workup

  1. customThe reaction is performed in a water/ice bath
  2. stirringThe reaction is stirred at 0° C. for 8 hours
  3. waitto stand at RT over night

Sources & evidence

ORD record
ord-6f989a21389d4c8b8420816143f6e655
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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