Water → HCID 54369541, compound

HRID 1003148Notes

Reaction equation

HRID 1003148 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH3:17].[C:18]1([B:24](F)F)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CCCCC.C1COCC1>[CH3:2][C:1]1[CH:4]=[CH:17][C:8]2[C:7](=[CH:16][CH:11]=[CH:10][CH:9]=2)[C:3]=1[B:24]([C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[CH3:17])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 962WaterHCID 757541-Bromo-2-methylnaphthaleneHCID 136201368-98-9HCID 178418306HCID 178418306, compound

Product 1

HCID 54369541HCID 54369541, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

27 ml of a 1.5 M solution of t-butyllithium in pentane are added over the course of 1.5 hours at -78° C. to a solution of 4.42 g (0.02 mol) of 1-bromo-2-methylnaphthalene in 40 ml of THF. The reaction mixture is stirred for 1 hour. 1.1 ml of phenyldifluoroborane (1.26 g, 0.01 mol) are added. The mixture is then allowed to warm to room temperature and is stirred for 2 hours more. The mixture is poured into 300 ml of water and the resulting suspension is filtered. The product is purified by chromatography (SiO2, hexane), to give 1.43 g (i.e. 39% of theory) of the borane as a white solid with a melting point of 208-209° C. The 1H-NMR shifts δ measured in CDCl3 are: 7.72 ppm (d,4,J=8.3 Hz), 7.53 ppm (d,2,J=8.6 Hz), 7.40-7.35 ppm (m,3), 7.25-7.15 ppm (m,6), 7.03 ppm (t,2,J=7 Hz) and 2.16 ppm (s,6).

Workup

  1. stirringis stirred for 2 hours more
  2. filtrationthe resulting suspension is filtered
  3. customThe product is purified by chromatography (SiO2, hexane)

Sources & evidence

ORD record
ord-b999c36b598547418cd4dd000ab10d61
Source dataset
uspto-grants-2000_04
Patent number
US06045974

Reaction notes

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