Water → 2-Benzyl-3-(4'-bromomethylbiphen-4-yl)benzofuran

HRID 2113188Notes

Reaction equation

HRID 2113188 reaction equation
[CH2:1]([C:8]1[O:9][C:10]2[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:31]P(Br)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>C(#N)C>[CH2:1]([C:8]1[O:9][C:10]2[CH:30]=[CH:29][CH:28]=[CH:27][C:11]=2[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][C:22]([CH2:25][Br:31])=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 70579Triphenylphosphine dibromideHCID 688199514'-(2-Benzylbenzofuran-3-yl)biphenyl-4-methanol

Product 1

HCID 596961782-Benzyl-3-(4'-bromomethylbiphen-4-yl)benzofuranYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4′-(2-benzylbenzofuran-3-yl)biphenyl-4-methanol (5.01 g, 12.7 mmol) in anhydrous acetonitrile (75 mL) was added dibromtriphenylphosphorane (5.45 g, 12.7 mmol) as a solid portionwise over 15 mins. The reaction was stirred for 2 hours (TLC control) and then poured into water (100 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to afford the title compound as an off-white solid (4.98 g, 87%): 1H NMR (CDCl3, 300 MHz): δ 7.70 (2H, m, Ar-H), 7.63 (4H, m, Ar-H), 7.50 (3H, m, Ar-H), 7.30 (4H, m, Ar-H), 7.25 (4H, m, Ar-H), 4.57 (2H, s, CH2Br), 4.26 (2H, PhCH2).

Workup

  1. extractionextracted with diethyl ether (3×100 mL)
  2. extractionThe combined extract
  3. washwas washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b5cf3e8035e145d1b3f1ac2f272146b5
Source dataset
uspto-grants-2009_04
Patent number
US07524878B2

Reaction notes

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