Boron tribromide → trans-4-Hydroxystilbene

HRID 2276282Notes

Reaction equation

HRID 2276282 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1245920P-Methoxystilbene

Product 1

HCID 5284650trans-4-HydroxystilbeneYield 43.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-5 °C

Procedure

To 210 mg (1 mmol) of (E)-4-methoxystilbene (4b) in 7 mL of CH2Cl2 was added 1.28 mL of 1M BBr3 (1.3 mmol) in dichloromethane at −10° C. The mixture was stirred for 4 h at −5° C. and quenched by pouring into cold water. The product was extracted with CH2Cl2, dried over anhydrous MgSO4 and chromatographed using 1:10 CH3OH:CH2Cl2 to afford 85 mg (43%) of 4a. mp 184-185° C.

Workup

  1. customquenched
  2. additionby pouring into cold water
  3. extractionThe product was extracted with CH2Cl2
  4. dry with materialdried over anhydrous MgSO4
  5. customchromatographed

Sources & evidence

ORD record
ord-a3ebcee1b39f412393865af02bbcf999
Source dataset
uspto-grants-2015_09
Patent number
US09132102B2

Reaction notes

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