Thionyl Chloride → alpha-(4-Bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride

HRID 1460080Notes

Reaction equation

HRID 1460080 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8](O)[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:10]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([Cl:26])[C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 53744634alpha-(4-Bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl alcohol

Product 1

HCID 22350043alpha-(4-Bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude benzhydryl alcohol (53.2 g, 135 mmol) was dissolved in 1000 mL of dichloromethane and 14.7 mL (202 mmol) of thionyl chloride was added dropwise. The solution was stirred overnight at room temperature and the solvent was removed under vacuum. The crude product was redissolved in 500 mL of toluene and the solvent again was removed under vacuum to eliminate excess thionyl chloride, providing crude α-(4-bromophenyl)-3-(tert-butyldimethylsilyloxy)benzyl chloride as a dark oil. NMR (200 MHz, CDCl3): δ 0.2 (s,6H); 1.0 (s,9H); 6.0 (s,1H); 6.78 (dd,J1 =1 Hz,J2 =8 Hz,1H); 6.9 (m,2H); 7.2 (t,J=8 Hz,2H); 7.27 and 7.47 (AB q,J=8 Hz,4H).

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe crude product was redissolved in 500 mL of toluene
  3. customthe solvent again was removed under vacuum

Sources & evidence

ORD record
ord-021cb87dcaed4857a4c5e91f33a68afa
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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