HRID1638754

反应详情

EQUATION

反应方程式

HRID 1638754 的结构方程式

AUXILIARIES

试剂、催化剂与溶剂

1

PROCEDURE

实验过程

Into a dry 250 milliliter round bottom flask equipped with a magnetic stirrer and nitrogen inlet was added 4-amino-2-bromo-3,6-dimethylphenol (11.94 grams, 55.3 mmol) prepared in Part B and dry dimethylsulfoxide (118 milliliters). Potassium t-butoxide (7.26 grams, 64.65 mmol) was added portionwise under nitrogen and the mixture was stirred at room temperature for 0.5 hours. Solid 3,4-dichloronitrobenzene (13.33 grams, 70.52 mmol) was then added and the reaction mixture was heated at 50° C. for 48 hours. After cooling the mixture was diluted with toluene and washed successively with saturated NH4Cl solution (3x) and with 5% NaOH solution until the aqueous washes remained colorless. This was followed by washes with water and brine, drying over Na2SO4 and solvent removal under reduced pressure to afford the crude product (9.4 grams) as a dark red-brown oil. Flash column chromatography on 650 grams of silica gel (3:1 hexane:ethyl acetate) afforded pure 3-bromo-4-(2 -chloro-4-nitrophenoxy)-2,5-dimethylaniline (4.7 grams, 12.6 mmol, 23%) as a yellow-brown solid. H'-NMR (CDCl3) 8.42 (d, J=2 Hz, 1H), 8.01 (d,d; J=2, 9 Hz; 1H), 6.55 (d, J=9 Hz, 1H), 6.58 (S, 1H), 3.73 (brS, 2H), 2.28 (S, 3H), 2.06 (S, 3H).

WORKUP

后处理

  1. customInto a dry 250 milliliter round bottom flask equipped with a magnetic stirrer and nitrogen inlet
  2. temperaturethe reaction mixture was heated at 50° C. for 48 hours
  3. temperatureAfter cooling the mixture
  4. washwashed successively with saturated NH4Cl solution (3x) and with 5% NaOH solution until the aqueous washes
  5. dry with materialdrying over Na2SO4 and solvent removal under reduced pressure
  6. customto afford the crude product (9.4 grams) as a dark red-brown oil