Methanol → 5-Bromo-2-methyl-2-phenylpentan-1-ol

HRID 239080

Reaction equation

HRID 239080 reaction equation
BrCCCCC(C)(C1C=CC(C)=CC=1)CO.[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22](OCC)=[O:23].[Li+].[BH4-].CO>C(Cl)Cl>[Br:17][CH2:18][CH2:19][CH2:20][C:21]([CH3:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:22][OH:23]

Participants

6

Reactant 4

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 111968926-Bromo-2-methyl-2-p-tolylhexan-1-olHCID 23431358Ethyl 5-bromo-2-methyl-2-phenyl-pentanoate

Product 1

HCID 113458925-Bromo-2-methyl-2-phenylpentan-1-olYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to the procedure given for the synthesis of 206e, 205b (23.70 g, 79.21 mmol) was reduced with LiBH4 (3.45 g, 158.4 mmol) and methanol (5.24 g, 163.5 mmol) in anhydrous CH2Cl2 (150 mL) to give 206b (20.0 g, 98%) as an oil. 1H NMR (CDCl3): δ 7.34-7.14 (m, 5 H), 3.60 (m, 1 H), 3.48 (m, 1 H), 3.29 (t, 2 H, J=6.0), 1.96-1.44 (m, 5 H), 1.32 (s, 3 H). 13C NMR (CDCl3): δ 144.25, 128.59, 126.71, 126.41, 72.44, 43.15, 37.06, 34.64, 27.58, 21.61. HRMS (LSIMS, nba): Calcd for C12H16Br (MH+-H2O): 239.0435, found: 239.0444.

Sources & evidence

ORD record
ord-4d171bc6f05a44ee8f0e1bd9010e9b23
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Linked notes

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