1,3-Dihydroisobenzofuran → 2-(Bromomethyl)benzyl alcohol

To a solution of 1M BBr3 in CH2Cl2 (49.2 mL, 49.2 mmol) cooled at 0° C. was added dropwise over 45 minutes a solution of phthalan (17.40 g, 142.6 mmol) in CH2Cl2 (30 mL). After the addition, the mixture was heated to reflux (oil bath) for 1 hour, then cooled to room temperature and quenched with water (50 mL). The mixture was washed with H2O (100 mL), 50% saturated NaHCO3 (100 mL), H2O (100 mL), brine, dried (MgSO4) and concentrated in vacuo to give a brownish solid, which was crystallized from EtOAc/hexane to afford 16.442 g of the title compound of this step as a light yellow crystalline compound. The mother liquor was concentrated and the residue crystallized (EtOAc/hexane) to yield an additional 6.30 g of the title compound of this step (total amount of product: 22.742 g, 80% yield).

1. additionAfter the addition
2. temperaturethe mixture was heated
3. temperatureto reflux (oil bath) for 1 hour
4. customquenched with water (50 mL)
5. washThe mixture was washed with H2O (100 mL), 50% saturated NaHCO3 (100 mL), H2O (100 mL), brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customto give a brownish solid, which
9. customwas crystallized from EtOAc/hexane

ORD record

ord-f1b04fbef0864dbb873769d0483bde93

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06235922B1