Diethyl Ether → HCID 86612829, compound

HRID 2076430Notes

Reaction equation

HRID 2076430 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[CH2:8][CH2:7][C:6]2([CH3:16])[CH3:15].[C:17]1([P:23]([C:30]2C=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH2:36](OCC)C>ClCCl>[Br-:1].[CH3:13][C:9]1([CH3:14])[CH2:8][CH2:7][C:6]([CH3:16])([CH3:15])[C:5]2[CH:4]=[C:3]([C:2]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[P+:23]([CH3:36])([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:12]=[CH:11][C:10]1=2

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 27355976-(Bromomethyl)-1,1,4,4-Tetramethyl-1,2,3,4-Tetrahydronaphthalene

Product 1

HCID 86612829HCID 86612829, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 250 mL round bottom flask was charged 6-(bromomethyl)-1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalene 8 (2.00 g, 7.11 mmol) in solution in 11 mL of dichloromethane. Triphenylphosphine (2.15 g, 8.18 mmol) was added via spatula at room temperature. The reaction mixture was stirred overnight at RT (16 h). Diethyl ether (200 mL) was added and the white precipitate formed was filtered and washed copiously with diethyl ether and dried in vacuo over P2O5. (5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphtalenyl)-methyl-triphenylphosphonium bromide 9 (3.40 g, 88% yield) was obtained as a white solid.

Workup

  1. customthe white precipitate formed
  2. filtrationwas filtered
  3. washwashed copiously with diethyl ether
  4. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-70797752ac974347bf9c6985f204787e
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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