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]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.
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