Chlorotrimethylsilane → 5-Bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-phenylmethanol
Reaction equation
[Li+].[BH4-].Cl[Si](C)(C)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=2[CH3:28])=[C:13]([CH:17]=1)[C:14](O)=[O:15]>C1COCC1>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[C:21]=2[CH3:28])=[C:13]([CH2:14][OH:15])[CH:17]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Into a dry 100 mL flask was weighed LiBH4 (0.55 g; 25.0 mmol). THF (25 mL) was added and the suspension was cooled to 0° C. To the chilled suspension was added chlorotrimethylsilane (6.36 mL; 50.0 mmol). Then solid 5-bromo-2-[2-(3-methoxy-2-methylphenyl)-ethyl]-benzoic acid 7 (4.37 g; 12.5 mmol) was added portion-wise, slowly enough to control bubbling of the mixture. After addition, the ice bath was removed and the suspension was stirred at ambient temperature overnight. The mixture was quenched by slowly adding methanol until the bubbling stopped and the solution turned clear. The solvents were evaporated and the residue was stirred in water, basified using 2.5 N NaOH solution and extracted with dichloromethane. The organic extracts were combined, dried over Na2SO4 and evaporated to obtain the compound 8 as a low-melting solid (4.19 g crude).
Workup
- customInto a dry 100 mL flask was weighed
- customslowly enough to control bubbling of the mixture
- additionAfter addition
- customthe ice bath was removed
- customThe mixture was quenched by slowly adding methanol until the bubbling
- customThe solvents were evaporated
- stirringthe residue was stirred in water
- extractionextracted with dichloromethane
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-ca48dd9606344e219b6188ee1df89276
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07582667B2
Reaction notes
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