2-Bromoanisole → HCID 18507125, compound

HRID 1633542Notes

Reaction equation

[Mg].Br[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[O:9][CH3:10].[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1>C1COCC1>[Br:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[CH:3]=2)[OH:17])=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of magnesium (2.4 g, 100 mmmol), in THF (20 mL) at room temperature was added dropwise a solution of bromoanisole (9.1 mL, 71.4 mmol) in THF (30 mL). The reaction mixture was stirred at room temperature for 2 h and at 60° C. for 2 h. The mixture was cooled to room temperature and a solution of 4-bromobenzaldehyde (13.2 g, 71.4 mmol) was added over 5 min. The reaction mixture was stirred at room temperature for 3 h and was quenched by addition of aqueous saturated ammonium chloride (NH4Cl) (30 mL). The aqueous layer was washed with ether (3×40 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography with hexanes/EtOAc (10:1) afforded 16.95 g of (4-bromo-phenyl)-(3-methoxy-phenyl)-methanol. 1HNMR (400 MHz, CDCl3) δ 7.46-7.41 (comp, 2H), 7.27-7.18 (comp, 3H), 6.91-6.87 (comp, 2H), 6.81-6.78 (m, 1H), 5.73 (s, 1H), 3.76 (s, 3H); MS (M+1) 294.2.

Workup

temperatureThe mixture was cooled to room temperature
stirringThe reaction mixture was stirred at room temperature for 3 h
customwas quenched by addition of aqueous saturated ammonium chloride (NH4Cl) (30 mL)
washThe aqueous layer was washed with ether (3×40 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customPurification by flash chromatography with hexanes/EtOAc (10:1)

Sources & evidence

ORD record: ord-cf9941b58d974d9b95fdba1c09593cc0
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503905B1

Reaction notes

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