Acetic Acid → HCID 14839521, compound

HRID 2260024Notes

Reaction equation

HRID 2260024 reaction equation
N[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:3]=1.C(O)(=O)C.[BrH:27].N([O-])=O.[Na+]>O>[Br:27][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[CH:14]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 260Hydrogen Bromide2×HCID 14839523HCID 14839523, compound2×HCID 23668193Sodium Nitrite

Product 1

HCID 14839521HCID 14839521, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
0 °C

Procedure

Ethyl 4-amino-2-(3,4-dimethoxyphenyl)benzoate (20.0 g; 0.066 mole; compound 252) and acetic acid (200 ml) are introduced into a 1000 ml three-necked flask. After dissolution, 47% strength hydrobromic acid (60 ml) is added, the mixture is cooled to 0° C. and then distilled water (150 ml) is added. Sodium nitrite (4.6 g; 0.066 mole) dissolved in water (30 ml) is poured in. Stirring is continued at between 0° and 5° C. for one hour, then the mixture is poured onto a solution of cuprous bromide (9.5 g; 0.066 mole) in 47% strength hydrobromic acid (100 ml). The reaction mixture is heated to 65% for one hour, then poured into water. The precipitate formed is filtered, rinsed with water and then dried in the air. Ethyl 4-bromo-2-(3,4-dimethoxyphenyl)benzoate (18.4 g; yield: 76.3%) is thus obtained, m.p. 53° C. (compound 250).

Workup

  1. additionis added
  2. additionis poured in
  3. temperatureThe reaction mixture is heated to 65% for one hour
  4. customThe precipitate formed
  5. filtrationis filtered
  6. washrinsed with water
  7. customdried in the air

Sources & evidence

ORD record
ord-81fe780311d843588015d9d0b10ca3ce
Source dataset
uspto-grants-1995_12
Patent number
US05475132

Reaction notes

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