Sulfuric Acid → HCID 18435271, compound

HRID 2304362Notes

Reaction equation

HRID 2304362 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[C:12]3[CH:19]=[CH:20][CH:21]=[CH:22][C:11]=3[C:10]3[CH:23]=[CH:24][CH:25]=[CH:26][C:9]2=3)=[CH:4][CH:3]=1.C([Li])CCC.[B:32]([O:37]C)(OC)[O:33]C.S(=O)(=O)(O)O>O1CCCC1.CCCCCC>[CH:19]1[C:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:8]([C:5]3[CH:4]=[CH:3][C:2]([B:32]([OH:37])[OH:33])=[CH:7][CH:6]=3)[C:9]3[CH:26]=[CH:25][CH:24]=[CH:23][C:10]=3[C:11]=2[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 8470Trimethyl borateHCID 9933189HCID 9933189, compoundHCID 178418339Butyllithium

Product 1

HCID 18435271HCID 18435271, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Ten point zero (10.0) grams (22.5 mmol) of 9-(4-iodophenyl)tribenz[b,d,f]azepin was dissolved in 50 ml of tetrahydrofuran, and the solution was cooled to −78° C. Fourteen point one (14.1) ml (22.5 mmol) of a 1.6 M hexane solution containing n-butyl lithium was dropwise added thereinto. After completion of the addition, the solution was stirred for 30 minutes, and then a tetrahydrofuran solution containing 2.8 g (22.5 mmol) of trimethyl borate was dropwise added thereto over about one hour. After completion of the addition, the solution was stirred for 1 hour, then the temperature was gradually raised to room temperature, and the solution was allowed to react for further two hours. Subsequently, a dilute sulfuric acid (3 ml of sulfuric acid and 50 ml of water) was added at 0° C. and hydrolysis was performed. The reaction solution was extracted with ethyl acetate, concentrated under reduced pressure, the obtained solid of boronic acid was recrystallized with toluene and purified, thereby 6.1 g of 4-(tribenz[b,d,f]azepin-9-yl)phenyl boronic acid was obtained (yield: 75%).

Workup

  1. additionwas dropwise added
  2. additionAfter completion of the addition
  3. additionwas dropwise added
  4. waitover about one hour
  5. additionAfter completion of the addition
  6. stirringthe solution was stirred for 1 hour
  7. temperaturethe temperature was gradually raised to room temperature
  8. customto react for further two hours
  9. customhydrolysis
  10. extractionThe reaction solution was extracted with ethyl acetate
  11. concentrationconcentrated under reduced pressure
  12. customthe obtained solid of boronic acid was recrystallized with toluene
  13. custompurified

Sources & evidence

ORD record
ord-d8a108d0ebfc4577beda3e28a0bf837a
Source dataset
uspto-grants-2002_08
Patent number
US06436558B1

Reaction notes

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