Methyl iodide → 2-(3-Bromophenyl)-2-methylpropyl methyl ether

HRID 2223402Notes

Reaction equation

HRID 2223402 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1.[CH3:15]I>C1COCC1.CCOCC>[Br:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][CH3:15])[CH:5]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128051212-(3-Bromophenyl)-2-methylpropan-1-ol

Product 1

HCID 671914112-(3-Bromophenyl)-2-methylpropyl methyl etherYield 91%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of NaH (0.22 g, 9.00 mmol, 95%) in THF (30 mL) was added dropwise at ambient temperature the solution of 2-(3-bromo-phenyl)-2-methyl-propan-1-ol (1.7 g, 7.46 mmol) in THF (10 mL). After 10 min MeI (0.8 mL, 15 mmol) was added and the mixture stirred for 3 h at ambient temperature. The mixture was diluted with ether and washed twice with water. Organic layer was separated and concentrated to obtain the desired product (1.64 g, 91%) as a clear oil. NMR (DMSO-d6): 7.52 (m, 1H), 7.40 (m, 2H), 7.26 (m, 1H), 3.38 (s, 2H), 3.20 (s, 3H), 1.12 (s, 6H). MS (DCI): 260 (M+NH4).

Workup

  1. washwashed twice with water
  2. customOrganic layer was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-50f21d46d9c045dc9f006f7ebe096648
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

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