Dimethylformamide → 5-Bromo-3,3,7-trimethyl-2,3-dihydro-benzofuran

HRID 402772

Reaction equation

[CH3:1][C:2](=[CH2:14])[CH2:3][O:4][C:5]1[C:10]([CH3:11])=[CH:9][C:8]([Br:12])=[CH:7][C:6]=1Br.CC([O-])=O.[K+].C(O[Na])=O.CN(C=O)C>[N+](CC)(CC)(CC)CC.[Cl-].O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Br:12][C:8]1[CH:9]=[C:10]([CH3:11])[C:5]2[O:4][CH2:3][C:2]([CH3:14])([CH3:1])[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

To a nitrogen flushed 100 mL round bottom flask were added 2,4-dibromo-6-methylphenyl 2-methylprop-2-en-1-yl ether (710 mg, 2.22 mmol), Pd(dppf)Cl2 (36 mg, 0.044 mmol), Et4NCl (490 mg, 2.66 mmol), KOAc (544 mg, 5.55 mmol), HCO2Na (181 mg, 2.66 mmol), DMF (20 mL) and water (1 mL). The reaction mixture was heated at 75° C. overnight. After cooling to room temperature, it was diluted with water and extracted with EtOAc/hexanes (1:3). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified on a silica gel column eluting with a gradient of 100% hexanes to 10% EtOAc/hexanes to give the title intermediate (110 mg, 70% purity) as light yellow liquid.

Workup

customTo a nitrogen flushed 100 mL round bottom flask
temperatureAfter cooling to room temperature
extractionextracted with EtOAc/hexanes (1:3)
dry with materialThe organic layer was dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on a silica gel column
washeluting with a gradient of 100% hexanes to 10% EtOAc/hexanes

Sources & evidence

ORD record: ord-9361579a0c8e451a83a487b13e3e2b32
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08742110B2

Linked notes

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