Dimethylformamide → 4-Bromo-1-(chloromethyl)-2-methylbenzene

HRID 2366512Notes

Reaction equation

HRID 2366512 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12]O)=[C:8]([CH3:14])[CH:7]=1.CN(C)C=O>ClCCl>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][Cl:3])=[C:8]([CH3:14])[CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 22280088(4-Bromo-2-methylphenyl)methanol

Product 1

HCID 200723584-Bromo-1-(chloromethyl)-2-methylbenzeneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add thionyl chloride (14.31 mL, 0.2 mol,) to a solution of (4-bromo-2-methyl-phenyl)methanol (32.9 g, 0.16 mol) in dichloromethane (200 mL) and dimethylformamide (0.025 mol, 2.0 mL) at 0° C. After 1 hour at room temperature pour the mixture into ice-water (100 g), extract with dichloromethane (300 mL), wash extract with 5% aq. sodium bicarbonate (30 mL) and brine (200 mL), dry over sodium sulfate, and concentrate under reduced pressure to give the crude title compound as a white solid (35.0 g, 0.16 mol). The material is used for the next step of reaction without further purification. 1H NMR (CDCl3): δ 2.38 (s, 3H), 4.52 (s, 2H), 7.13-7.35 (m, 3H).

Workup

  1. extractionextract with dichloromethane (300 mL)
  2. washwash
  3. extractionextract with 5% aq. sodium bicarbonate (30 mL) and brine (200 mL)
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-fd8fc332579e4cb783f8ac81bf59eb94
Source dataset
uspto-grants-2014_04
Patent number
US08697849B2

Reaction notes

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