Hexane → HCID 21069658, compound

HRID 1371236Notes

Reaction equation

HRID 1371236 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][C:5]([C:17]2[CH:22]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:20]([Br:32])=[CH:19][C:18]=2I)=[C:4](I)[CH:3]=1.CCCCCC.[Br-].[Mg+2].[Br-].[CH:44]([C:47]1[CH:52]=[C:51]([CH:53]([CH3:55])[CH3:54])[CH:50]=[C:49]([CH:56]([CH3:58])[CH3:57])[C:48]=1[B:59](OC)OC)([CH3:46])[CH3:45]>O1CCCC1>[Br:1][C:2]1[C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])=[CH:6][C:5]2[C:17]3[CH:22]=[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[C:20]([Br:32])=[CH:19][C:18]=3[B:59]([C:48]3[C:49]([CH:56]([CH3:57])[CH3:58])=[CH:50][C:51]([CH:53]([CH3:55])[CH3:54])=[CH:52][C:47]=3[CH:44]([CH3:46])[CH3:45])[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 8058HexaneHCID 82241Magnesium BromideHCID 10934694Dimethyl [2,4,6-tri(propan-2-yl)phenyl]boronateHCID 21069659HCID 21069659, compound

Product 1

HCID 21069658HCID 21069658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.0 g of 4,4′-dibromo-2,2′-diiodo-5,5′-dioctyloxy-1,1′-biphenyl synthesized as above was put in a 100 ml flask in an atmosphere of nitrogen and 20 ml of tetrahydrofuran was added to dissolve the same. Then, the tetrahydrofuran solution was cooled to −90° C. and 3.4 ml of 1.6M hexane solution was added dropwise. After 1-hour stirring, a solution of 1.5 g of magnesium bromide in 20 ml of tetrahydrofuran was added, warmed to room temperature, and stirred for 1 hour. The mixture was cooled again to −90° C., and 1.01 g of (2,4,6-triisopropylphenyl)dimethoxyborane was added. After warming, the mixture was allowed to react under reflux for 12 hours.

Workup

  1. additionwas added
  2. dissolutionto dissolve the same
  3. stirringstirred for 1 hour
  4. temperatureThe mixture was cooled again to −90° C.
  5. temperatureAfter warming
  6. customto react
  7. temperatureunder reflux for 12 hours

Sources & evidence

ORD record
ord-e46395004e664909bfd2812dc56a087b
Source dataset
uspto-grants-2007_01
Patent number
US07157154B2

Reaction notes

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