Allyl bromide → 1-[(Allyloxy)methyl]-2-iodobenzene

To a THF (200 ml) solution of 2-iodo-benzyl alcohol (25 g, 107 mmol), at r.t., was added the NaH (5.12 g, 128 mmol) in small portions. After complete addition of the NaH the allyl bromide (11.1 ml , 128 mmol) was added via syringe. The mixture was stirred overnight at room temperature. The resulting white heterogeneous mixture was quenched with H20 (100 ml) and diluted with 300 ml of Et2O followed by washing with H2O (2×100 ml) and brine (1×100 ml). The organic layer was dried over MgSO4 and concentrated in vacuo to yield 31 g of 1-[(allyloxy)methyl]-2-iodobenzene as a faint yellow oil. HRMS (ESI+) calcd for C10H11IO m/z 273.9857 (M+H)+. Found 273.9855.

1. additionwas added via syringe
2. customThe resulting white heterogeneous mixture was quenched with H20 (100 ml)
3. additiondiluted with 300 ml of Et2O
4. washby washing with H2O (2×100 ml) and brine (1×100 ml)
5. dry with materialThe organic layer was dried over MgSO4
6. concentrationconcentrated in vacuo

ORD record

ord-084404e0005949d687e8e2d59509e101

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544717B2