13 c nmr cdcl 3 u03b433 83 38 74 40 75 nme 2 112 82 2c ar 126 87 129 41 2c ar 149 67 ir neat 2900 1613 1519 1352 1204 808 hrms esi m z calcd for c 10 h 14 brn m h 228 0388 found 228 0380 m h in a dried 25 mnl round bottomed flask under argon was taken a solution of the appropriate alcohol 1 mmol in ether acetonitrile 3 1 10 ml triphenyl phosphine 3 equiv was added to this solution followed by imidazole 3 equiv and then bromine 3 equiv and the mixture was stirred at room temperature for 2h monitoring the progress by tlc the reaction mixture was filtered and washed with ether 2 u00d7 15 ml the organic layers were combined washed with brine 1 u00d7 25 ml dried over mgso 4 and filtered the combined solvents were evaporated under reduced pressure the residue was purified by flash chromatography on silica gel eluting with 1 ethyl acetate hexanes to afford the corresponding bromides 41b yield 92 1 h nmr cdcl 3 u03b42 48 s 3h 3 12 t 2h j 7 6 hz 3 54 t 2h j 7 6 hz 7 14 d 2h j 8 11 hz 7 22 d 2h j 8 12 hz 13 c nmr cdcl 3 u03b416 42 33 47 39 25 127 35 2c ar 129 62 2c ar 136 18 137 40 ir neat 2921 1495 1437 1095 809 gcms ei m z.