Benzyl Bromide → HCID 67523754, compound

HRID 2190932Notes

Reaction equation

[OH:1][C:2]1[C:7]2[C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[H-].[Na+]>CN(C=O)C>[CH2:15]([O:1][C:2]1[C:7]2[C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:13])[O:11][C:6]=2[CH:5]=[CH:4][CH:3]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5-hydroxy-2,2-dimethyl-benzo[1,3]dioxin-4-one (Uchiyama M. et al Org. Lett. 2006, 8(24), 5517-5520) (2.0 g, 10.4 mmol) and benzyl bromide (1.78 g, 10.4 mmol) in DMF in an ice bath was added sodium hydride (60% dispersed in mineral oil, 624 mg, 15.6 mmol). Resulting mixture was stirred at 0° C. for 10 min and then at rt for 6 h. Reaction mixture was quenched with water (250 mL), neutralized using 1 N HCl to pH=6-7 and extracted with EtOAc (2×). Combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. Crude product was triturated with hexanes (50 mL). Solid was collected and dried in vacuo to provide the title compound 2.5 g. 1H NMR (200 MHz, CDCl3): δ (ppm)=7.54 (m, 2H), 7.37 (m, 4H), 6.57 (m, 2H), 5.25 (s, 2H), 1.71 (s, 6H).

Workup

customResulting mixture
waitat rt for 6 h
customReaction mixture
customwas quenched with water (250 mL)
extractionextracted with EtOAc (2×)
washCombined organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customCrude product was triturated with hexanes (50 mL)
customSolid was collected
customdried in vacuo

Sources & evidence

ORD record: ord-6a6437b19baa452380e8dcc2f1b034b3
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324405B2

Reaction notes

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