Acetyl bromide → 2-Docosyloxy-9-(4-chlorophenyl)-9-bromofluorene

HRID 1047392Notes

Reaction equation

HRID 1047392 reaction equation
[CH2:1]([O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)(O)[C:26]=2[CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C([Br:48])(=O)C>C(Cl)(Cl)Cl>[CH2:1]([O:23][C:24]1[CH:36]=[CH:35][C:34]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([C:38]3[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][CH:39]=3)([Br:48])[C:26]=2[CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 10482Acetyl bromideHCID 469277222-Docosyloxy-9-(4-chlorophenyl)-9-fluorenol

Product 1

HCID 469277232-Docosyloxy-9-(4-chlorophenyl)-9-bromofluoreneYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Docosyloxy-9-(4-chlorophenyl)-9-fluorenol (200 mg, 0.33 mmol) prepared in the above-mentioned 1-2 was dissolved in chloroform (2 ml), acetyl bromide (48 μl, 0.65 mmol) was added dropwise and the mixture was stirred for 1 hour. After completion of the reaction, the solvent was evaporated, and the residue was precipitated with acetonitrile (2 ml) to give 2-docosyloxy-9-(4-chlorophenyl)-9-bromofluorene (209 mg, 0.31 mmol, 95%).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. customthe residue was precipitated with acetonitrile (2 ml)

Sources & evidence

ORD record
ord-c240f77da4b54a5bbdeba56100600be0
Source dataset
uspto-grants-2013_10
Patent number
US08569453B2

Reaction notes

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