Acetyl bromide → 9-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-bromofluorene

HRID 1047402Notes

Reaction equation

HRID 1047402 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(O)[C:20]3[CH:19]=[C:18]([O:21][CH2:22][CH:23]4[CH2:28][CH:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:26]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH:25]([O:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH3:85])[CH2:24]4)[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.C([Br:90])(=O)C>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([Br:90])[C:20]3[CH:19]=[C:18]([O:21][CH2:22][CH:23]4[CH2:28][CH:27]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH:26]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH:25]([O:67][CH2:68][CH2:69][CH2:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH2:80][CH2:81][CH2:82][CH2:83][CH2:84][CH3:85])[CH2:24]4)[CH:17]=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 469266539-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol

Product 1

HCID 469266549-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-bromofluoreneYield 386.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

9-(4-Chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-fluorenol (62.0 mg, 51.2 μmol) was dissolved in chloroform (2 mL), acetyl bromide (13 μmol, 172 μmol) was added, and the mixture was stirred at room temperature for 1 hours. After evaporation of the solvent, acetonitrile was added to the residue to allow crystallization to give 9-(4-chlorophenyl)-2-(3,4,5-tris(octadecyloxy)-cyclohexylmethoxy)-9-bromofluorene (63.9 mg, 50.2 μmol, 98%). δ=0.88 (9H, t, J=6.6 Hz, OC18H37 C18-H) 1.1-1.9 (101H, br, Cyclohexyl C1,2,6-H, OC18H37 C2-17-H) 3.16 (2H, d, J=10.3 Hz, Cyclohexyl C3,5-H) 3.46 (4H, m, 3,5-OC18H37 C1-H) 3.68 (2H, t, J=6.7 Hz, 4-OC18H37 C1-H) 3.82 (2H, m, fl-O—CH2—) 3.92 (1H, s, Cyclohexyl C4-H) 6.90 (1H, d, J=8.3 Hz, fl C3-H) 6.96 (1H, s, fl C1-H) 7.18-7.26 (3H, m,Ph C3,5-H, fl C7-H) 7.34 (1H, t, J=7.1 Hz, fl C6-H) 7.43 (1H, d, J=7.6 Hz, fl C8-H) 7.48 (2H, d, J=8.7 Hz, Ph C2,6-H) 7.57 (2H, m, fl C4,5-H)

Workup

  1. customAfter evaporation of the solvent, acetonitrile
  2. additionwas added to the residue
  3. customcrystallization

Sources & evidence

ORD record
ord-2f194298c2bb4ebbb3f7ab7a0c3f5980
Source dataset
uspto-grants-2013_10
Patent number
US08569453B2

Reaction notes

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