3-Aminophenol → 2-Bromo-N-(3-hydroxyphenyl)acetamide

HRID 1679607Notes

Reaction equation

HRID 1679607 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[Na+].[Br:14][CH2:15][C:16](Br)=[O:17]>C(O)(=O)C>[OH:8][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[NH:1][C:16](=[O:17])[CH2:15][Br:14]

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 61147Bromoacetyl bromideHCID 517045Sodium Acetate

Product 1

HCID 127641052-Bromo-N-(3-hydroxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
10 °C

Procedure

m-Aminophenol, 66.5 g. (0.61 mole), is dissolved in 500 ml. of a 50/50 (v/v) mixture of glacial acetic acid and saturated sodium acetate solution. The mixture is cooled to approximately 10° C. and 200 g. (0.99 mole) of bromoacetyl bromide is added dropwise. The temperature is maintained between 15° and 20° C. When addition is complete, the mixture is stirred while cooling until the temperature is about 5° C. The product is filtered off, washed successively with cold water, saturated sodium bicarbonate solution and finally two portions of water. The product is dried under vacuum. The yield of the title compound is 121 g. (86 percent of theory), m.p. 167°-170° C.

Workup

  1. dissolution(0.61 mole), is dissolved in 500 ml
  2. temperatureThe temperature is maintained between 15° and 20° C
  3. additionWhen addition
  4. temperaturewhile cooling until the temperature
  5. customis about 5° C
  6. filtrationThe product is filtered off
  7. washwashed successively with cold water, saturated sodium bicarbonate solution and finally two portions of water
  8. customThe product is dried under vacuum

Sources & evidence

ORD record
ord-f7ad2ebb555e449eaea38376e281e050
Source dataset
uspto-grants-1978_03
Patent number
US04081474

Reaction notes

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