Dimethylformamide → 5-bromo-6-methoxy-2,3-dihydro-1H-indene

HRID 1063253Notes

Reaction equation

HRID 1063253 reaction equation
CI.[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][C:5]=1[OH:13].[C:14]([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH3:14][O:13][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:4]=1[Br:3])[CH2:10][CH2:9][CH2:8]2.[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH2:10]2)=[CH:6][C:5]=1[OH:13]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 156453446-Bromo-2,3-dihydro-1H-inden-5-ol

Product 2

HCID 152482825-bromo-6-methoxy-2,3-dihydro-1H-indeneYield 74%HCID 156453446-Bromo-2,3-dihydro-1H-inden-5-olYield 19%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
51 °C

Procedure

Four oven dried 40 mL vials with Teflon lined caps were used in parallel for the reaction. The sealed vials were used to avoid loss of MeI. Each of the the vials was loaded with a fourth of 6-bromoindan-5-ol (12.01 g, 56.36 mmol), K2CO3 (15.58 g, 112.72 mmol), DMF (147.5 mL) and MeI (14.03 mL, 225.45 mmol) respectfully. The vials were sealed and heated on the orbital shaker for a total of 11 hours at 51° C. The reactions in the four vials were combined, poured in water and extracted twice with ethyl acetate. The organics were combined, dried with Na2SO4, filtered and concentrated to give 12.6 grams of a crude yellow oil. The crude was purified using the in two batches (120 g columns, 5% ethyl acetate). Like fractions were combined to give 9.53 grams (74%) of 6-bromo-2,3-dihydro-1H-inden-5-yl methyl ether as a white solid and 2.29 grams (19%) of recovered 6-bromoindan-5-ol. IR (diffuse reflectance) 2958, 2468, 2428, 2415, 2350, 2337, 1482, 1466, 1392, 1311, 1278, 1260, 865, 835, 733 cm−1. Anal. Calcd for C10H11BrO: C, 52.89; H, 4.88; Br, 35.18. Found: C, 52.87; H, 4.79; N, 0.21. Found: Br, 35.27. X-Ray supports the structure.

Workup

  1. dry with materialFour oven dried 40 mL vials with Teflon lined caps
  2. customwere used in parallel for the reaction
  3. customThe vials were sealed
  4. extractionextracted twice with ethyl acetate
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 12.6 grams of a crude yellow oil
  9. customThe crude was purified

Sources & evidence

ORD record
ord-21d46df51fc646efaffcf4a301244a16
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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