Boron tribromide → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 2103320Notes

Reaction equation

HRID 2103320 reaction equation
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(Cl)Cl.O>C(Cl)Cl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 2668644-(4-Methoxyphenoxy)biphenylHCID 21908982Water methylene chloride

Product 1

HCID 105634264-(4'-Hydroxyphenoxy)biphenylYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

4-(4-Methoxy-phenoxy)-biphenyl (1.0 g, 3.6 mmol) in anhydrous CH2Cl2 (10 mL) was cooled to −78° C. and 1M boron tribromide (10.8 mL, 10.8 mmol) in CH2Cl2 was added dropwise over period of 20 min under nitrogen. The resulting mixture was stirred at −78° C. for 2 h and at rt for 1 h. Then it was cooled to 0° C. and poured slowly over 1:1 mixture of CH2Cl2/water. CH2Cl2 layer was separated, washed with water, brine, dried over anhydrous MgSO4 and concentrated. The crude product was purified using silica gel flash chromatography (20% EtOAc/Hexane) to obtain the product as yellow solid (265 mg, 28%): MS; m/z 260.9 (M−H); 1H NMR (400 MHz, DMSO-d6); δ 6.79-6.82 (m, 1H), 6.91-6.98 (m, 2H), 7.30-7.49 (m, 4H), 7.60-7.68 (m, 6H), 8.36 (s, 1H).

Workup

  1. temperatureThen it was cooled to 0° C.
  2. customCH2Cl2 layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-ee7013d83b0548e185cca76221fb9650
Source dataset
uspto-grants-2009_08
Patent number
US07576102B2

Reaction notes

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