Water → 4-(3-Iodostyryl)phenol

HRID 1297536Notes

Reaction equation

HRID 1297536 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 11013106(E)-1-iodo-3-[2-(4-methoxyphenyl)ethenyl]benzene

Product 1

HCID 109142344-(3-Iodostyryl)phenolYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8 (350 mg, 1.00 mmol) in CH2Cl2 (200 mL) was added BBr3 (10 mL, 1M in hexane) dropwise at −78° C. in a dry ice-acetone bath. The mixture was allowed to warm up to room temperature. Water was added while the reaction mixture was cooled at 0° C. in an ice bath. The mixture was extracted with CH2Cl2. The organic phase was dried and filtered. The filtrate was purified by flash chromatography (EtOAc: Hex, 1:9) to give 9 (296 mg, 92%). 1H NMR (200 MHz, CDCl3): δ 4.81 (s, 1H), 6.83 (d, J=16.17 Hz, 1H), 6.84 (m, 2H), 7.03 (d, J=16.32 Hz, 1H), 7.06 (t, J=7.8 Hz, 1H), 7.36–7.57 (m, 4H), 7.84 (s, 1H); 13C NMR (50 MHz, CDCl3): δ 94.75, 115.67, 124.96, 125.49, 128.09, 129.48, 129.87, 130.25, 135.01, 135.96, 139.90, 155.53; HRMS: m/z Calcd for C14H11IO: 321.9855; Found: 321.9840.

Workup

  1. temperaturewas cooled at 0° C. in an ice bath
  2. extractionThe mixture was extracted with CH2Cl2
  3. customThe organic phase was dried
  4. filtrationfiltered
  5. customThe filtrate was purified by flash chromatography (EtOAc: Hex, 1:9)

Sources & evidence

ORD record
ord-adb7058c1d3e43ed8cf41ff964039ec3
Source dataset
uspto-grants-2007_07
Patent number
US07250525B2

Reaction notes

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