Water → HCID 59015237, compound

HRID 446639Notes

Reaction equation

HRID 446639 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:19]2[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=2)=[CH:4][CH:3]=1.C([Li])CCC.C(O[B:38]1[O:42][C:41]([CH3:44])([CH3:43])[C:40]([CH3:46])([CH3:45])[O:39]1)(C)C.O>C1COCC1.C(Cl)(Cl)Cl>[CH:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[N:8]([C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[C:5]1[CH:4]=[CH:3][C:2]([B:38]2[O:39][C:40]([CH3:45])([CH3:46])[C:41]([CH3:43])([CH3:44])[O:42]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 23083309HCID 23083309, compoundHCID 178418339Butyllithium

Product 1

HCID 59015237HCID 59015237, compoundYield 77.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

8.5 g (20 mmol) of (4-bromophenyl)dinaphthalene-2-ylamine was dissolved in 100 ml of THF and was cooled to −78° C. 9.6 ml (24 mmol) of 2.5M n-butyllithium was added slowly to the THF solution and maintained at the same temperature as above for an hour to allow reaction. 4.4 g (24 mmol) of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added to the reaction solution, and was maintained at the same temperature as above for an hour. The reaction solution was heated to room temperature (RT) and stirred for 24 hours. Water was added to end the reaction. 300 ml of chloroform was added to the solution and washed with 200 ml of water. The resulting organic layer was dried with anhydride magnesium sulfate. 7.3 g of dinaphthalen-2-yl-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolane-2-yl)phenyl]amine (intermediate B) was obtained through silica chromatography with a yield of 77%.

Workup

  1. temperaturemaintained at the same temperature as above for an hour
  2. customreaction
  3. temperaturewas maintained at the same temperature as above for an hour
  4. temperatureThe reaction solution was heated to room temperature (RT)
  5. customthe reaction
  6. washwashed with 200 ml of water
  7. dry with materialThe resulting organic layer was dried with anhydride magnesium sulfate

Sources & evidence

ORD record
ord-04a290deff8643f9b33170f10d71c554
Source dataset
uspto-grants-2013_07
Patent number
US08481174B2

Reaction notes

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