2-Bromophenol → HCID 20090600, compound

HRID 275189Notes

Reaction equation

HRID 275189 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:17]([CH3:22])([CH3:21])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]=2[CH:12]=1.CC1(C)CCC(C)(C)C2C=C(COC3C=CC(C(O)=O)=CC=3C3C=CC=CC=3)C=CC1=2>>[CH3:21][C:17]1([CH3:22])[CH2:16][CH2:15][C:14]([CH3:24])([CH3:23])[C:13]2[CH:12]=[C:11]([CH2:10][O:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Br:1])[CH:20]=[CH:19][C:18]1=2

Participants

4

Reactant 3

HCID 72442-BromophenolHCID 28008916-(Chloromethyl)-1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthaleneHCID 22558771HCID 22558771, compound

Product 1

HCID 20090600HCID 20090600, compoundYield 89%

Procedure

2-Bromophenol (1.50 g., 8.70 mmol) is alkylated with 2-chloromethyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene) (18a) (2.05 g., 8.70 mmol) in a similar manner as described in Example 26 (for the synthesis of 44) to afford 2-[5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl]methoxy-bromobenzene (50) (2.88 g., 7.72 mmol, 89%): chromatographed on silica gel using EtOAc/hexane to afford a clear oil; 1H NMR (300 MHz, CDCl3) δ 7.57 (dd, J=2, 8 Hz, 1H, ArH), 7.45 (d, J=2 Hz, 1H, ArH), 7.32 (d, J=8 Hz, 1H, ArH), 7.25 (m, 2H, ArH, 6.98 (dd, J=2, 8 Hz, 1H, ArH), 6.83 (dd, J=8, 8 Hz, 1H, ArH), 5.09 (s, 2H, ArCH2O), 1.70 (s, 4H, CH2CH2), 1.29 (s, 6H, 2×CH3), 1.28 (s, 6H, 2×CH3) .

Sources & evidence

ORD record
ord-97bf36416257496fa94f4987dd2ea543
Source dataset
uspto-grants-1995_02
Patent number
US05391817

Reaction notes

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