Bromotrimethylsilane → 1,3-Dichloro-2-{2-[4-(bromomethyl)phenoxy]ethoxy}-5-methylbenzene

HRID 2194863Notes

Reaction equation

HRID 2194863 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14]O)=[CH:10][CH:9]=1.C[Si]([Br:26])(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([Cl:21])[C:3]=1[O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][Br:26])=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 67447508{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}methanol

Product 1

HCID 584884381,3-Dichloro-2-{2-[4-(bromomethyl)phenoxy]ethoxy}-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of {4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}methanol from II.1, step 3 (1 eq.) in CH2Cl2 (0.1M) at room temperature was added a solution of trimethyl silyl bromide (1.05 eq.) in CH2Cl2 (1.0M). The final mixture was stirred 1 h at room temperature and then concentrated in vacuo. To the resulting suspension was added silica gel and the mixture was evaporated in vacuo. Purification by column chromatography on silica gel, eluting with Hex/Et2O 5%, afforded the desired compound as a crystalline white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the resulting suspension was added silica gel
  3. customthe mixture was evaporated in vacuo
  4. customPurification by column chromatography on silica gel
  5. washeluting with Hex/Et2O 5%

Sources & evidence

ORD record
ord-9fc6e859b1e0452fa7ec827092049ff6
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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