Boron tribromide → 2-(4-Hydroxyphenyl)-6-(4-nonylphenyl)benzothiazole

HRID 1243268Notes

Reaction equation

HRID 1243268 reaction equation
B(Br)(Br)Br.C([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[S:25][C:26]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=4)[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:20][CH:19]=1)CCCCCCCCCCC>ClCCl>[OH:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[S:25][C:26]3[CH:32]=[C:31]([C:33]4[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])=[CH:35][CH:34]=4)[CH:30]=[CH:29][C:27]=3[N:28]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 219245242-(4-Dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazole

Product 1

HCID 1357617792-(4-Hydroxyphenyl)-6-(4-nonylphenyl)benzothiazoleYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Boron tribromide (0.53 cm3, 5.65×10−3 mol) was added dropwise to a cooled (0° C.) stirred solution of 2-(4-dodecyloxyphenyl)-6-(4-nonylphenyl)benzothiazole (2.25 g, 3.76×10−3 mol) in dichloromethane (100 cm3). The reaction mixture was stirred at room temperature overnight, then poured onto an ice/water mixture (200 g) and stirred (30 min). The reaction mixture was extracted with dichloromethane (2×75 cm3) and the combined organic layers were washed with brine (2×100 cm3) and dried (MgSO4). After filtration the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel, ethyl acetate:hexane 1:1] followed by recrystallisation from ethyl acetate to yield 1.25 g (77.3%) of the desired product.

Workup

  1. stirringstirred (30 min)
  2. extractionThe reaction mixture was extracted with dichloromethane (2×75 cm3)
  3. washthe combined organic layers were washed with brine (2×100 cm3)
  4. dry with materialdried (MgSO4)
  5. filtrationAfter filtration the solvent
  6. customwas removed under reduced pressure
  7. customthe residue was purified by column chromatography [silica gel, ethyl acetate:hexane 1:1]
  8. customfollowed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-33520a08346448e58f6074d2f382d4e6
Source dataset
uspto-grants-2006_10
Patent number
US07118787B2

Reaction notes

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