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

HRID 873296Notes

Reaction equation

HRID 873296 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6](OCC)=[O:7].[Li+].[BH4-].CO>C(Cl)Cl>[Br:1][CH2:2][CH2:3][CH2:4][C:5]([CH3:17])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:6][OH:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 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. NMR (CDCl3): δ 7.34-7.14 (m, 5H), 3.60 (m, 1H), 3.48 (m, 1H), 3.29 (t, 2H, J=6.0), 1.96-1.44 (m, 5H), 1.32 (s, 3H). 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-36d389cbcdd146ec915e0603e9e93c77
Source dataset
uspto-grants-2015_03
Patent number
US08975300B2

Reaction notes

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