Water → 5-(Bromomethyl)-2,3-dihydrobenzofuran

HRID 1636607Notes

Reaction equation

HRID 1636607 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10]O)=[CH:9][C:4]=2[CH2:3][CH2:2]1.P(Br)(Br)[Br:13].O>O1CCCC1>[Br:13][CH2:10][C:8]1[CH:7]=[CH:6][C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24614Phosphorus tribromideHCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanol

Product 1

HCID 220048075-(Bromomethyl)-2,3-dihydrobenzofuranYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2,3-dihydrobenzofuran-5-yl)methanol (29.0 g, 0.193 mol) in tetrahydrofuran (150 mL) was added phosphorous tribromide (34.8 g, 0.129 mol) under ice/salt-cooling. The mixture was stirred for 20 minutes and then poured into water. The mixture was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated to afford the title compound (yield 27.6 g, 91%).

Workup

  1. temperaturesalt-cooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-8df52201aef24870888f02370db34145
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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