Boron tribromide → HCID 70819230, compound

HRID 1525751Notes

Reaction equation

HRID 1525751 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][C:24]=2[C:26]2[CH:31]=[C:30]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:29]([O:38]C)=[CH:28][C:27]=2[CH3:40])[CH:19]=[CH:18][CH:17]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:8][C:6]1[C:5]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:3]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][C:24]=3[C:26]3[CH:31]=[C:30]([C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C:29]([OH:38])=[CH:28][C:27]=3[CH3:40])[CH:19]=[CH:18][CH:17]=2)=[C:2]([CH3:1])[CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 70819337HCID 70819337, compound

Product 1

HCID 70819230HCID 70819230, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,8-bis(2′-methyl-4′-methoxy-5′-phenylphenyl)naphthalene, 6, (0.14 g, 0.28 mmol) in 10 mL of anhydrous CH2Cl2 at 0° C., BBr3 (1.67 mL, 1.67 mmol) was added dropwise and the mixture was stirred for sixteen hours at room temperature. The reaction was carefully quenched with isopropyl alcohol followed by addition of water, and extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated in vacuo. Purification by flash chromatography on silica gel (CH2Cl2) afforded 0.12 g of 2 (0.25 mmol, 89%) as a white solid.

Workup

  1. customThe reaction was carefully quenched with isopropyl alcohol
  2. additionfollowed by addition of water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel (CH2Cl2)

Sources & evidence

ORD record
ord-c50e0655c7d64f09940b452c98800514
Source dataset
uspto-grants-2015_07
Patent number
US09085511B2

Reaction notes

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